bluuebunny/crossref_metadata_2025 huggingface dataset:
2,3,5‐Triphenylisoxazolidine
Authors: Brüning Ingrid , Grashey Rudolf , Hauck Hans , Huisgen Rolf , Seidl Helmut
Published: November 2003

2,3,5‐Triphenylisoxazolidine

intermediate: N,α‐diphenylnitrone

product: 2,3,5,5‐tetraphenylisoxazolidine

product: ethyl 2,3‐diphenyl‐5‐methylisoxazolidine‐4‐carboxylate

product: 2,3,5‐Triphenylisoxazolidine
1,2,3‐Benzothiadiazole 1,1‐Dioxide
Authors: Wittig G. , Hoffmann R. W.
Published: November 2003

1,2,3‐Benzothiadiazole 1,1‐dioxide

intermediate: 2‐nitrobenzenesulfinic acid

intermediate: sodium 2‐aminobenzenesulfinate

product: 1,2,3‐benzothiadiazole 1,1‐dioxide
Cyclohexylidenecyclohexane
Authors: Turro Nicholas J. , Leermakers Peter A. , Vesley George F.
Published: November 2003

Cyclohexylidenecyclohexane

intermediate: 15 g. (0.068 mole) of dispiro[5.1.5.1]tetradecane‐7,14‐dione

product: cyclohexylidenecyclohexane
2‐Cyclohexyloxyethanol
Authors: Daignault Ronald A. , Eliel E. L.
Published: November 2003

2‐Cyclohexyloxyethanol

intermediate: 1,4‐Dioxaspiro[4.5]decane

product: 2‐Cyclohexyloxyethanol
3,5‐Dinitro‐
o
‐Tolunitrile
Authors: Olah George A. , Kuhn Stephen J.
Published: November 2003

3,5‐Dinitro‐
o
‐tolunitrile

reactant: 22 ml. (22 g., 1.10 moles) of cold, liquid, anhydrous hydrogen fluoride

intermediate: nitronium tetrafluoroborate

product:
3,5‐Dinitro‐o‐tolunitrile
Diphenylcyclopropenone
Authors: Breslow R. , Posner J.
Published: November 2003

Diphenylcyclopropenone

intermediate:
α,α′‐Dibromodibenzyl ketone

reactant: 100 ml. of triethylamine

product: diphenylcyclopropenone
Ethyl
p
‐Dimethylaminophenylacetate
Authors: Romanelli Michael G. , Becker Ernest I.
Published: November 2003

Ethyl
p
‐dimethylaminophenylacetate

product: ethyl
p
‐dimethylaminophenylacetate
Phenylcyclopropane
Authors: Petersen R. J. , Skell P. S.
Published: November 2003

Phenylcyclopropane

product: phenylcyclopropane
2‐Phenyl‐5‐Oxazolone
Authors: VandenBerg G. E. , Harrison J. B. , Carter H. E. , Magerlein B. J.
Published: November 2003

2‐Phenyl‐5‐oxazolone

solvent: Skellysolve B

product: 2‐phenyl‐5‐oxazolone
3(5)‐Aminopyrazole
Authors: Dorn H. , Zubek A.
Published: November 2003

3(5)‐Aminopyrazole

intermediate: β‐cyanoethylhydrazine

intermediate: 183 g. (1.00 mole) of 3‐amino‐3‐pyrazoline sulfate

intermediate: 191 g. (0.80 mole) of 3‐imino‐1‐(
p
‐tolylsulfonyl)‐pyrazolidine

byproduct: sodium
p
‐toluenesulfinate

product: 3(5)‐aminopyrazole
3‐Benzoyloxycyclohexene
Authors: Pedersen Knud , Jakobsen Preben , Lawesson Sven‐Olov
Published: November 2003

3‐Benzoyloxycyclohexene

product: 3‐benzoyloxycyclohexene
Bicyclo[2.2.1]Hepten‐7‐One
Authors: Gassman P. G. , Marshall J. L.
Published: November 2003

Bicyclo[2.2.1]hepten‐7‐one

product: bicyclo[2.2.1]hepten‐7‐one
3‐Bromopyrene
Authors: Gumprecht W. H.
Published: November 2003

3‐Bromopyrene

reactant: 8.08 g. (0.040 mole) of pyrene

product: 3‐Bromopyrene
t
‐Butyl Diazoacetate
Authors: Regitz Manfred , Hocker Jürgen , Liedhegener Annemarie
Published: November 2003

t
‐Butyl diazoacetate

intermediate:
p
‐toluenesulfonyl azide

solvent: 75.8 g. (0.75 mole) of previously distilled triethylamine

intermediate: 92.6 (0.50 mole) of
t
‐butyl α‐diazoacetoacetate

byproduct:
p
‐toluenesulfonamide

product:
t
‐butyl diazoacetate
2‐
n
‐Butyl‐2‐methylcyclohexanone
Authors: Boatman S. , Harris T. M. , Hauser C. R.
Published: November 2003

2‐
n
‐Butyl‐2‐methylcyclohexanone

reactant: 123 g. (1.10 moles) of 2‐methylcyclohexanone

reactant: 81.4 g. (1.10 moles) of ethyl formate

intermediate: Sodio‐2‐formyl‐6‐methylcyclohexanone

reactant: 28.2 g. (0.21 mole) of
n
‐butyl bromide

product: 2‐
n
‐butyl‐2‐methylcyclohexanone

byproduct: 2‐formyl‐6‐
n
‐butyl‐6‐methylcyclohexanone

product: 2,2‐Dimethylcyclohexanone

product: 2‐benzyl‐2‐methylcyclohexanone
1‐Cyanobenzocyclobutene
Authors: Skorcz J. A. , Kaminski F. E.
Published: November 2003

1‐Cyanobenzocyclobutene

product: 1‐cyanobenzocyclobutene

product: ethyl 2‐(
o
‐chlorobenzyl)cyanoacetate

product: 2‐(
o
‐chlorobenzyl)cyanoacetic acid

product:
o
‐chlorohydrocinnamonitrile
Di‐
t
‐Butyl Nitroxide
Authors: Hoffmann A. K. , Feldman A. M. , Gelblum E. , Henderson A.
Published: November 2003

Di‐
t
‐butyl nitroxide

product: di‐
t
‐butyl nitroxide
1,3‐Dihydroisoindole
Authors: Bornstein J. , Shields J. E. , Boisselle A. P.
Published: November 2003

1,3‐Dihydroisoindole

product: 1,3‐dihydroisoindole
7,7‐Dimethoxybicyclo[2.2.1]heptene
Authors: Gassman P. G. , Marshall J. L.
Published: November 2003

7,7‐Dimethoxybicyclo[2.2.1]heptene

intermediate: 5,5‐dimethoxy‐1,2,3,4‐tetrachlorocyclopentadiene

intermediate: 106 g. (0.36 mole) of 7,7‐dimethoxy‐1,2,3,4‐tetrachlorobicyclo[2.2.1]hept‐2‐ene

product: 7,7‐dimethoxybicyclo[2.2.1]heptene
1,1‐Diphenylcyclopropane
Authors: Jorgenson M. J. , Thacher A. F.
Published: November 2003

1,1‐Diphenylcyclopropane

intermediate: β‐phenylcinnamic acid

product: diphenylcyclopropane

R = C
6
H
5
, R′ = CH
3
Ar = C
6
H
5

R = R′ = CH
3
Ar = m‐CF
3
C
6
H
4

R = R′ = CH
3
Ar = C
6
H
5

R = R′ = H Ar = C
6
H
5
a

R = R′ = CH
3
Ar = 3,4‐Cl
2
C
6
H
3
D
‐2‐Oxo‐7,7‐dimethyl‐1‐vinylbicyclo[2.2.1]heptane
Authors: Fischer Nikolaus , Opitz G.
Published: November 2003

D
‐2‐Oxo‐7,7‐dimethyl‐1‐vinylbicyclo[2.2.1]heptane

reactant: 13.0 g. (0.052 mole) of
D
‐camphor‐10‐sulfonyl chloride

byproduct: Triethylamine hydrochloride

intermediate: episulfone

product:
D
‐2‐Oxo‐7,7‐dimethyl‐1‐vinylbicyclo[2.2.2]heptane
2‐Phenylindazole
Authors: Cadogan J. I. G. , Mackie R. K.
Published: November 2003

2‐Phenylindazole

intermediate:
o
‐nitrobenzalaniline

byproduct: Triethyl phosphite

byproduct: triethyl phosphate

product: 2‐phenylindazole
2‐
t
‐Butyl‐3‐phenyloxazirane
Authors: Emmons W. D. , Pagano A. S.
Published: November 2003

2‐
t
‐Butyl‐3‐phenyloxazirane

intermediate: N‐
t
‐butylbenzaldimine

product: 2‐
t
‐butyl‐3‐phenyloxazirane
2‐Chlorothiirane 1,1‐dioxide
Authors: Paquette Leo A. , Wittenbrook Lawrence S.
Published: November 2003

2‐Chlorothiirane 1,1‐dioxide

intermediate: Chloromethanesulfonyl chloride

product: 2‐chlorothiirane 1,1‐dioxide
Crotyl Diazoacetate
Authors: Blankley C. John , Sauter Frederick J. , House Herbert O.
Published: November 2003

Crotyl diazoacetate

intermediate:Glyoxylic acid p‐toluenesulfonylhydrazone.

intermediate:p‐toluenesulfonylhydrazone of glyoxylic acid chloride

solvent: petroleum ether (b.p. 30–60°; about 50 ml.

product:Crotyl diazoacetate.

reactant: 7.80 g. (0.077 mole) of redistilled triethylamine
cis‐Cyclododecene
Authors: Ohno Masaji , Okamoto Masaru
Published: November 2003

cis‐Cyclododecene

solvent: 350‐ml. portions of petroleum ether

product:cis‐cyclododecene

byproduct:cis,trans‐1,5‐cyclododecadiene
Dimethyl Cyclohexanone‐2,6‐Dicarboxylate
Authors: Balasubrahmanyam S. N. , Balasubramanian M.
Published: November 2003

Dimethyl cyclohexanone‐2,6‐dicarboxylate

reactant: Cyclohexanone (20.0 g., 0.204 mole)

product: Dimethyl cyclohexanone‐2, 6‐dicarboxylate
Diphenylcarbodiimide, Method
II
Authors: Rajagopalan S. , Advani B. G. , Talaty C. N.
Published: November 2003

Diphenylcarbodiimide, Method II

intermediate: N‐sulfinylaniline

reactant: 50 g. (0.41 mole) of benzaldoxime

solvent: 150 ml. of petroleum ether

intermediate: benzohydroxamoyl chloride

intermediate: triethylamine hydrochloride

product: diphenyl carbodiimide
3‐Isoquinuclidone
Authors: Pearlman W. M.
Published: November 2003

3‐Isoquinuclidone

catalyst: 2 g. of 10% rhodium‐0.1% palladium on carbon

intermediate:
cis
‐ and
trans
‐4‐aminocyclohexanecarboxylic acid

product: 3‐isoquinuclidone
Reduction of Conjugated Alkenes with Chromium(II) Sulfate: Diethyl Succinate
Authors: Zurqiyah A. , Castro C. E.
Published: November 2003

Reduction of conjugated alkenes with chromium(II) sulfate: diethyl succinate

product: diethyl succinate
m
‐Trifluoromethyl‐N,N‐Dimethylaniline
Authors: Sheppard William A.
Published: November 2003

m
‐Trifluoromethyl‐N,N‐Dimethylaniline

product:
m
‐Trifluoromethyl‐N,N‐dimethylaniline
tert
‐Butyl Azidoformate
Authors: Insalaco Michael A. , Tarbell D. Stanley
Published: November 2003

tert
‐Butyl azidoformate

reactant: 20.6 g. (0.120 mole) of pure diethyl phosphorochloridate

solvent: 120 ml. of anhydrous dimethyl sulfoxide

reactant: 8.1 g (0.10 mole) of powdered potassium azide

intermediate: 25.4 g. (0.100 mole) of
tert
‐butylcarbonic diethylphosphoric anhydride

product:
tert
‐butyl azidoformate
m
‐Chloroperbenzoic Acid
Authors: McDonald Richard N. , Steppel Richard N. , Dorsey James E.
Published: November 2003

m
‐Chloroperbenzoic acid

reactant: 52.5 g. (0.300 mole) of
m
‐chlorobenzoyl chloride

product:
m
‐chloroperbenzoic acid
α,α′‐Dibromodibenzyl Sulfone
Authors: Carpino Louis A. , McAdams Louis V.
Published: November 2003

α,α′‐Dibromodibenzyl sulfone

solvent: 250–300 ml. of ligroin

intermediate: α‐bromophenylacetic acid

intermediate: 24.9 g. (0.0824 mole) of crude α,α′‐diphenylthiodiglycolic acid

product: α,α′‐dibromodibenzyl sulfone

intermediate: dibenzyl sulfide
2,4‐Dimethoxybenzonitrile
Authors: Lohaus G.
Published: November 2003

2,4‐Dimethoxybenzonitrile

product: 2,4‐dimethoxybenzonitrile
Hexafluoroacetone Imine
Authors: Middleton W. J. , Carlson H. D.
Published: November 2003

Hexafluoroacetone imine

reactant: 462 g. (2.78 moles) of hexafluoroacetone

product: Hexafluoroacetone imine
cis
‐2‐Phenylcyclopropanecarboxylic Acid
Authors: Kaiser Carl , Weinstock Joseph , Olmstead M. P.
Published: November 2003

cis
‐2‐Phenylcyclopropanecarboxylic acid

reactant: 163 g. (1.57 moles) of styrene

intermediate: 155 g. (0.816 mole) of ethyl
cis
‐ and
trans
‐2‐phenylcyclopropanecarboxylate

product:
cis
‐2‐phenylcyclopropanecarboxylic acid

product:
trans
‐2‐Phenylcyclopropanecarboxylic acid
Preparation of Hydrazones: Acetophenone Hydrazone
Authors: Newkome G. R. , Fishel D. L.
Published: November 2003

Preparation of hydrazones: acetophenone hydrazone

intermediate: acetophenone
N,N
‐dimethylhydrazone

product: acetophenone hydrazone
2‐Thiophenethiol
Authors: Jones E. , Moodie I. M.
Published: November 2003

2‐Thiophenethiol

product: 2‐thiophenethiol

product: 2‐Chloro‐5‐thiophenethiol

product: 3‐thiophenethiol

product: thiophenol
Aldehydes by Oxidation of Terminal Olefins with Chromyl Chloride: 2,4,4‐Trimethylpentanal
Authors: Freeman Fillmore , DuBois Richard H. , McLaughlin Thomas G.
Published: November 2003

Aldehydes by oxidation of terminal olefins with chromyl chloride: 2,4,4‐trimethylpentanal

catalyst: 158 g. (1.02 moles) of freshly distilled chromyl chloride

product: 2,4,4‐trimethylpentanal

product: 4,4‐Dimethyl‐2‐neopentylpentanal

product: 2‐Phenylpropanal

product: Diphenylacetaldehyde
Aldehydes from Acid Chlorides by Modified
R
osenmund Reduction: 3,4,5‐Trimethoxybenzaldehyde
Authors: Rachlin A. I. , Gurien H. , Wagner D. P.
Published: November 2003

Aldehydes from acid chlorides by modified Rosenmund reduction: 3,4,5‐trimethoxybenzaldehyde

product: 3,4,5‐trimethoxybenzaldehyde

product: 3,4‐dimethylbenzaldehyde

product: 3‐benzyloxy‐4,5‐dimethoxybenzaldehyde

product: 3‐methoxy‐4‐nitrobenzaldehyde
Aldehydes from Aromatic Nitriles: 4‐Formylbenzenesulfonamide
Authors: van Es T. , Staskun B.
Published: November 2003

Aldehydes from aromatic nitriles: 4‐formylbenzenesulfonamide

product: 4‐formylbenzenesulfonamide

product: C
6
H
5
CHO

product: 4‐ClC
6
H
4
CHO

product: 4‐CH
3
OC
6
H
4
CHO

product: 2‐C
10
H
7
CHO

product: C
6
H
5
CHO

product: 2‐CH
3
C
6
H
4
CHO

product: 2‐ClC
6
H
4
CHO

product: 2‐CH
3
OC
6
H
4
CHO

product: 2,6‐(CH
3
O)
2
C
6
H
3
CHO

product: C
6
H
5
CHCHCHO
Aldehydes from 2‐Benzyl‐4,4,6‐Trimethyl‐5,6‐Dihydro‐1,3(4
H
)‐Oxazine: 1‐Phenylcyclopentanecarboxaldehyde
Authors: Politzer Ieva R. , Meyers A. I.
Published: November 2003

Aldehydes from 2‐benzyl‐4,4,6‐trimethyl‐5,6‐dihydro‐1,3(4
H
)‐oxazine: 1‐phenylcyclopentanecarboxaldehyde

reactant: 21.7 g. (0.100 mole) of 2‐benzyl‐4,4,6‐trimethyl‐5,6‐dihydro‐1,3(4
H
)‐oxazine

reactant: 1,4‐Dibromobutane (23.8 g., 0.110 mole)

intermediate: 2‐(1‐phenylcyclopentyl)‐4,4,6‐trimethyl‐5,6‐dihydro‐1,3(4
H
)‐oxazine

intermediate: 2‐(1‐
Phenylcyclopentyl
)‐4,4,6‐
trimethyltetrahydro
‐1,3‐
oxazine

solvent: 150‐ml. portions of petroleum ether

product: 1‐phenylcyclopentanecarboxaldehyde
Amines from Mixed Carboxylic‐Carbonic Anhydrides: 1‐Phenylcyclopentylamine
Authors: Kaiser Carl , Weinstock Joseph
Published: November 2003

Amines from Mixed Carboxylic‐Carbonic Anhydrides: 1‐Phenylcyclopentylamine

reactant: 38.0 g. (0.200 mole) of 1‐phenylcyclopentanecarboxylic acid

product: 1‐phenylcyclopentylamine
Aziridines from β‐Iodocarbamates: 1,2,3,4‐Tetrahydronaphthalene(1,2)imine
Authors: Heathcock C. H. , Hassner A.
Published: November 2003

Aziridines from β‐iodocarbamates: 1,2,3,4‐tetrahydronaphthalene(1,2)imine

product: 1,2,3,4‐Tetrahydronaphthalene(1,2)imine
Bicyclo[1.1.0]butane
Authors: Lampman Gary M. , Aumiller James C.
Published: November 2003

Bicyclo[1.1.0]butane

product: bicyclo[1.1.0]butane

byproduct: cyclobutene
3‐Chlorocyclobutanecarboxylic Acid
Authors: Lampman Gary M. , Aumiller James C.
Published: November 2003

3‐Chlorocyclobutanecarboxylic acid

reactant: 172.8 g. (1.200 moles) of 1,1‐cyclobutanedicarboxylic acid

byproduct: cyclobutanecarboxylic acid

product: 3‐chlorocyclobutanecarboxylic acid
Ethyl Pyrrole‐2‐Carboxylate
Authors: Bailey Denis M. , Johnson Robert E. , Albertson Noel F.
Published: November 2003

Ethyl pyrrole‐2‐carboxylate

intermediate: 2‐
Pyrrolyl trichloromethyl ketone

product: ethyl pyrrole‐2‐carboxylate
Hydrogenation of Aromatic Nuclei: 1‐Decalol
Authors: Meyers A. I. , Beverung W. N. , Gault R.
Published: November 2003

Hydrogenation of aromatic nuclei: 1‐Decalol

product:
cis,cis
‐1‐decalol

product: 2‐Decalol

product:
cis
‐2‐Methylhexahydrobenzofuran

product:
cis
‐2,2‐Dimethylhexahydrobenzofuran

product: 3‐Hydroxycyclohexanecarboxylic acid

product: 4‐Methoxycyclohexanol

product: 1,4‐Cyclohexanediol

product: 1,3‐Cyclohexanediol
4‐Phenyl‐1,2,4‐Triazoline‐3,5‐Dione
Authors: Cookson R. C. , Gupte S. S. , Stevens I. D. R. , Watts C. T.
Published: November 2003

4‐Phenyl‐1,2,4‐triazoline‐3,5‐dione

intermediate: 52 g. (0.50 mole) of ethyl hydrazinecarboxylate in 550 ml. of dry benzene

intermediate: 4‐phenyl‐1‐carbethoxysemicarbazide

intermediate: 4‐phenylurazole

product: 4‐(4‐nitrophenyl)urazole

product: 4‐
tert
‐butylurazole

product: 4‐Benzalaminourazole

product: 4‐benzalamino‐1,2,4‐triazoline‐3,5‐dione

product: 4‐Phenyl‐1,2,4‐triazoline‐3,5‐dione
Phenylation with Diphenyliodonium Chloride: 1‐Phenyl‐2,4‐Pentanedione
Authors: Hampton K. Gerald , Harris Thomas M. , Hauser Charles R.
Published: November 2003

Phenylation with diphenyliodonium chloride: 1‐phenyl‐2,4‐pentanedione

reactant: 40.0 g. (0.400 mole) of 2,4‐pentanedione

product: 1‐phenyl‐2,4‐pentanedione

byproduct: iodobenzene

product: 1‐phenyl‐1,3‐butanedione

product: 2,4‐heptanedione

product: 2,4‐nonanedione

product: 2,4‐tridecanedione

product: 3,5‐heptanedione

product: 1‐(4‐chlorophenyl)‐2,4‐pentanedione

product: 4‐(4‐methylphenyl)‐1‐phenyl‐1,3‐butanedione

product: 1‐(4‐methylphenyl)‐2,4‐nonanedione
Quadricyclane
Authors: Smith Claibourne D.
Published: November 2003

Quadricyclane

reactant: 180 g. (1.96 moles) of bicyclo[2.2.1]hepta‐2,5‐diene

product: quadricyclane
1,2,3,4‐Tetrahydro‐β‐Carboline
Authors: Ho Beng T. , Walker K. E.
Published: November 2003

1,2,3,4‐Tetrahydro‐β‐carboline

reactant: 25 g. (0.13 mole) of tryptamine hydrochloride

product: 1,2,3,4‐tetrahydro‐β‐carboline
Thiophenols from Phenols: 2‐Naphthalenethiol
Authors: Newman Melvin S. , Hetzel Frederick W.
Published: November 2003

Thiophenols from phenols: 2‐naphthalenethiol

reactant: 21.6 g. (0.150 mole) of 2‐naphthol

reactant: 24.8 g. (0.201 mole) ofN,N‐dimethylthiocarbamyl chloride

intermediate:O‐2‐naphthyl dimethylthiocarbamate

product: 2‐naphthalenethiol
Trimethyloxonium Tetrafluoroborate
Authors: Curphey T. J.
Published: November 2003

Trimethyloxonium tetrafluoroborate

product: trimethyloxonium tetrafluoroborate
Aldehydes from Primary Alcohols by Oxidation with Chromium Trioxide: Heptanal
Authors: Collins J. C. , Hess W. W.
Published: November 2003

Aldehydes from primary alcohols by oxidation with chromium trioxide: heptanal

intermediate: dipyridine chromium(VI) oxide

reactant: 5.8 g. (0.050 mole) of 1‐heptanol

product: heptanal

product: 2‐methoxybenzaldehyde

product: 4‐nitrobenzaldehyde
Benzyl Chloromethyl Ether
Authors: Connor D. S. , Klein G. W. , Taylor G. N. , Boeckman R. K. , Medwid J. B.
Published: November 2003

Benzyl chloromethyl ether

product: benzyl chloromethyl ether

product: benzyl bromomethyl ether
3‐Butyl‐2‐methylhept‐1‐en‐3‐ol
Authors: Pearce P. J. , Richards D. H. , Scilly N. F.
Published: November 2003

3‐Butyl‐2‐methylhept‐1‐en‐3‐ol

product: 3‐butyl‐2‐methyl‐1‐hepten‐3‐ol

solvent: petroleum ether

product: 3‐Pentanol

product: Benzhydrol

product: Tri‐
n
‐butyl carbinol

product: 5‐Nonanol

product: 1‐Penten‐3‐ol

product: 3‐Methyl‐4‐heptanol
Formation and Photochemical
W
olff Rearrangement of Cyclic α‐Diazo Ketones:
D
‐Norandrost‐5‐en‐3β‐ol‐16‐Carboxylic Acids
Authors: Wheeler Thomas N. , Meinwald J.
Published: November 2003

Formation and photochemical Wolff rearrangement of cyclic α‐diazo ketones:
D
‐norandrost‐5‐en‐3β‐ol‐16‐carboxylic acids

intermediate: 16‐
Oximinoandrost
‐5‐
en
‐3β‐
ol
‐17‐
one

intermediate: 7.50 g. (0.0239 mole) of 16‐diazoandrost‐5‐en‐3β‐ol‐17‐one

product:
D
‐norandrost‐5‐en‐3β‐ol‐16α‐carboxylic acid

product: methyl
D
‐norandrost‐5‐en‐3β‐ol‐16β‐carboxylate
Hydrogenolysis of Carbon‐Halogen Bonds with Chromium(II)‐en Perchlorate: Naphthalene from 1‐Bromonaphthalene
Authors: Wade Ruth S. , Castro C. E.
Published: November 2003

Hydrogenolysis of carbon‐halogen bonds with chromium(II)‐en perchlorate: naphthalene from 1‐bromonaphthalene

reactant: 6.01 g. (0.100 mole) of ethylenediamine

reactant: 1.66 g. (0.00802 mole) of 1‐bromonaphthalene

product: naphthalene
Macrocyclic Polyethers: Dibenzo‐18‐crown‐6 Polyether and Dicyclohexyl‐18‐crown‐6 Polyether
Authors: Pedersen Charles J.
Published: November 2003

Macrocyclic polyethers: Dibenzo‐18‐crown‐6 polyether and dicyclohexyl‐18‐crown‐6 polyether

reactant: 222 g. (1.55 moles) of bis(2‐chloroethyl) ether

product: Dibenzo‐18‐crown‐6 polyether

product: dicyclohexyl‐18‐crown‐6 polyethers

solvent: petroleum ether (b.p. 30–60°, approximately 200 ml. was required)

solvent: dichloromethane–petroleum ether

intermediate: complex of potassium acetate with isomer B of dicyclohexyl‐18‐crown‐6 polyether
2‐Methyl‐2‐Nitrosopropane and its Dimer
Authors: Calder A. , Forrester A. R. , Hepburn S. P.
Published: November 2003

2‐Methyl‐2‐nitrosopropane and its dimer

product: 2‐methyl‐2‐nitropropane

intermediate: N‐tert‐
Butylhydroxylamine

intermediate: 2‐
Methyl
‐2‐
nitrosopropane
Reaction of Aryl Halides with π‐Allylnickel Halides: Methallylbenzene
Authors: Semmelhack Martin F. , Helquist Paul M.
Published: November 2003

Reaction of aryl halides with π‐allylnickel halides: methallylbenzene

reactant: 50.8 g. (38.5 ml., 0.298 mole) of nickel carbonyl

solvent: 250 ml. of petroleum ether

product: methallylbenzene

reactant: Methallyl bromide

intermediate: π‐methallylnickel bromide

byproduct: 1% 2,5‐dimethyl‐1,5‐hexadiene

byproduct: biphenyl

product: β,β‐dimethylstyrene
Substitution of Aryl Halides with Copper(
I
) Acetylides: 2‐Phenylfuro[3,2‐
b
]Pyridine
Authors: Owsley D. C. , Castro C. E.
Published: November 2003

Substitution of aryl halides with copper(I) acetylides: 2‐phenylfuro[3,2‐
b
]pyridine

reactant: copper(I) phenylacetylide

product: 2‐
Phenylfuro
[3,2‐b]
pyridine
2‐Acetyl‐6‐Methoxynaphthalene
Authors: Arsenijevic L. , Arsenijevic V. , Horeau A. , Jacques J.
Published: November 2003

2‐acetyl‐6‐methoxynaphthalene

product: 2‐acetyl‐6‐methoxynaphthalene

reactant: 2‐Methoxynaphthalene (Matheson, Coleman and Bell)
3,5‐Dinitrobenzaldehyde
Authors: Siggins J. E. , Larsen A. A. , Ackerman J. H. , Carabateas C. D.
Published: November 2003

3,5‐Dinitrobenzaldehyde

reactant: 115.0 g. (0.4989 mole) of 3,5‐dinitrobenzoyl chloride

solvent: 500 ml. of dry diglyme

product: 3,5‐dinitrobenzaldehyde
β‐Hydroxy Esters from Ethyl Acetate and Aldehydes or Ketones: Ethyl 1‐Hydroxycyclohexylacetate
Authors: Rathke Michael W.
Published: November 2003

β‐Hydroxy Esters from Ethyl Acetate and Aldehydes or Ketones: Ethyl 1‐hydroxycyclohexylacetate

reactant: 42.2 g. (0.263 mole) of hexamethyldisilazane

byproduct: hexamethyldisiloxane

product: Ethyl 1‐hydroxycyclohexylacetate
2,2‐(Trimethylenedithio)Cyclohexanone
Authors: Woodward R. B. , Pachter I. J. , Scheinbaum M. L.
Published: November 2003

2,2‐(Trimethylenedithio)cyclohexanone

intermediate: 1‐
Pyrrolidinocyclohexene

product: 2,2‐
(Trimethylenedithio)cyclohexanone

reactant: Trimethylene dithiotosylate
N
‐Alkylindoles from the Alkylation of Sodium Indolide in Hexamethylphosphoric Triamide: 1‐Benzylindole
Authors: Rubottom George M. , Chabala John C.
Published: November 2003

N
‐alkylindoles from the alkylation of sodium indolide in hexamethylphosphoric triamide: 1‐benzylindole

product: 1‐benzylindole
Preparation of Vinyl Trifluoromethanesulfonates: 3‐Methyl‐2‐buten‐2‐yl Triflate
Authors: Stang Peter J. , Dueber Thomas E.
Published: November 2003

Preparation of Vinyl Trifluoromethanesulfonates: 3‐Methyl‐2‐buten‐2‐yl Triflate

intermediate: trifluoromethanesulfonic anhydride

reactant: 2.78 g. (0.0352 mole) of anhydrous pyridine

solvent: 10 ml. of anhydrous
n
‐pentane

product: 3‐methyl‐2‐buten‐2‐yl triflate

byproduct: 3‐methyl‐1‐buten‐2‐yl triflate

product: CH
2
C(CH
3
)OSO
2
CF
3

product:
cis
and
trans
C
2
H
5
CHC(C
2
H
5
)OSO
2
CF
3

product: CH
2
C(OSO
2
CF
3
)C(CH
3
)
3

product: CH
2
C(C
6
H
5
)OSO
2
CF
3

product: CH
2
C(OSO
2
CF
3
)CH
2
(CH
2
)
2
CH
3

product: CH
2
C(OSO
2
CF
3
)CH(CH
3
)
2

product: C
6
H
5
C(CH
3
)C(CH
3
)OSO
2
CF
3
(
cis
, 18%;
trans
, 51%) + C
6
H
5
CH(CH
3
)C(OSO
2
CF
3
)CH
2
(31%)

product: C
6
H
5
C(CH
3
)C(CH
3
)OSO
2
CF
3
(
trans
, 80%;
cis
, 20%)

product: (CH
3
)
2
CC(CH
3
)OSO
2
CF
3
(
1
, 70%) + (CH
3
)
2
CHC(OSO
2
CF
3
)CH
2
(
2
, 30%)

product:
1
(90%) + 
2
(10%)
Macrocyclic Diimines: 1,10‐Diazacycloöctadecane
Authors: Park Chung Ho , Simmons Howard E.
Published: November 2003

Macrocyclic diimines: 1,10‐Diazacycloöctadecane

intermediate: 1,10‐diazacycloöctadecane‐2,9‐dione

product: 1,10‐diazacycloöctadecane
Tri‐
tert
‐Butylcyclopropenyl Tetrafluoroborate
Authors: Ciabattoni J. , Nathan E. C. , Feiring A. E. , Kocienski P. J.
Published: November 2003

Tri‐
tert
‐Butylcyclopropenyl tetrafluoroborate

reactant: 74.6 g. (0.700 mole) of 1‐chloro‐2,2‐dimethylpropane

reactant: 71.7 g. (0.533 mole) of
tert
‐butylacetyl chloride

intermediate: dineopentyl ketone

intermediate: α,α′‐
Dibromodineopentyl ketone

intermediate: 20.0 g. (0.120 mole) of di‐
tert
‐butylcyclopropenone

product: tri‐
tert
‐butylcyclopropenyl tetrafluoroborate
Addition of Organolithium Reagents to Allyl Alcohol: 2‐Methyl‐1‐Hexanol
Authors: Crandall J. K. , Rojas A. C.
Published: November 2003

Addition of Organolithium Reagents to Allyl Alcohol: 2‐Methyl‐1‐Hexanol

reactant: 7.25 g. (0.125 mole) of 2‐propen‐1‐ol

reactant: 1.16 g. (0.0100 mole) ofN,N,N′,N′‐tetramethyl‐1,2‐ethanediamine

product: 2‐methyl‐1‐hexanol
Alkenes
via
H
ofmann Elimination: Use of Ion‐Exchange Resin for Preparation of Quaternary Ammonium Hydroxides: Diphenylmethyl Vinyl Ether
Authors: Kaiser Carl , Weinstock Joseph
Published: November 2003

Alkenes
via
Hofmann elimination: use of ion‐exchange resin for preparation of quaternary ammonium hydroxides: diphenylmethyl vinyl ether

product: diphenylmethyl vinyl ether

reactant: 2‐(diphenylmethoxy)‐
N,N
‐dimethylethylamine, b.p. 150–165° (2 mm.),G. Rieveschl, Jr., (to Parke Davis and Company), U.S. Pat. 2,421,714 (1947) [Chem. Abstr., 41, 5550 h (1947)]. obtained from Searle Chemicals, Inc., or from the hydrochloride, m.p. 161–162°, which is available commercially from Gane's Chemical Works, Inc., New York, New York, under the generic name, diphenhydramine

intermediate: 2‐(diphenylmethoxy)‐
N,N
‐dimethylethylamine methiodide
3‐(4‐Chlorophenyl)‐5‐(4‐Methoxyphenyl)Isoxazole
Authors: Perkins Matilda , Beam Charles F. , Dyer Morgan C. D. , Hauser Charles R.
Published: November 2003

3‐(4‐Chlorophenyl)‐5‐(4‐methoxyphenyl)isoxazole

reactant: 16.96 g. (0.1000 mole) of 4‐chloroacetophenone oxime

product: 3‐(4‐chlorophenyl)‐5‐(4‐methoxyphenyl)isoxazole
4,4′‐Dimethyl‐1,1′‐Biphenyl
Authors: Elsom L. F. , McKillop Alexander , Taylor Edward C.
Published: November 2003

4,4′‐Dimethyl‐1,1′‐biphenyl

reactant: 42.7 g. (30.5 ml., 0.250 mole) of 4‐bromotoluene

intermediate: (4‐methylphenyl)magnesium bromide

product: 4,4′‐dimethyl‐1,1′‐biphenyl

product: biphenyl

product: 4,4′‐dimethoxy‐1,1′‐biphenyl

product: 3,3′‐dimethyl‐1,1′‐biphenyl

product: 3,3′,4,4′‐tetramethyl‐1,1′‐biphenyl

product: 4,4′‐dichloro‐1,1′‐biphenyl

product: 4,4′‐difluoro‐1,1′‐biphenyl
Free‐Radical Cyclization: Ethyl 1‐Cyano‐2‐Methylcyclohexanecarboxylate
Authors: Julia Marc , Maumy Michel
Published: November 2003

Free‐radical cyclization: ethyl 1‐cyano‐2‐methylcyclohexanecarboxylate

intermediate: (
E
)‐4‐hexen‐1‐yl
p
‐toluenesulfonate

solvent: 400 ml. of anhydrous
N,N
‐dimethylformamide

reactant: 68 g. (0.60 mole) of ethyl cyanoacetate

intermediate: ethyl (
E
)‐2‐cyano‐6‐octenoate

product: ethyl 1‐cyano‐2‐methylcyclohexanecarboxylate
Phase‐Transfer Alkylation of Nitriles: 2‐Phenylbutyronitrile
Authors: Makosza M. , Jończyk A.
Published: November 2003

Phase‐transfer alkylation of nitriles: 2‐phenylbutyronitrile

product: 2‐phenylbutyronitrile

byproduct: α‐phenylcinnamonitrile

product: (C
6
H
5
)
2
CHCH(C
6
H
5
)CN

product: (C
6
H
5
)
2
C(CH
2
CH
2
Br)CN
Secondary and Tertiary Alkyl Ketones from Carboxylic Acid Chlorides and Lithium Phenylthio(Alkyl)Cuprate Reagents:
tert
‐Butyl Phenyl Ketone
Authors: Posner Gary H. , Whitten Charles E.
Published: November 2003

Secondary and tertiary alkyl ketones from carboxylic acid chlorides and lithium phenylthio(alkyl)cuprate reagents:
tert
‐butyl phenyl ketone

reactant: 8.81 g. (0.0801 mole) of freshly distilled thiophenol

reactant: 2.81 g. (0.0200 mole) of freshly distilled benzoyl chloride

product:
tert
‐butyl phenyl ketone

byproduct:
tert
‐butyl benzoate (from lithium
tert
‐butoxide;)
Acylamidoalkyl Acetophenones from Substituted Phenethylamines: 2‐(2‐Acetamidoethyl)‐4,5‐Dimethoxyacetophenone
Authors: Brossi A. , Dolan L. A. , Teitel S.
Published: November 2003

Acylamidoalkyl acetophenones from substituted phenethylamines: 2‐(2‐acetamidoethyl)‐4,5‐dimethoxyacetophenone

reactant: 54.0 g. (0.243 mole) of
N
‐acetylhomoveratrylamine

intermediate: 6,7‐dimethoxy‐1‐methyl‐3,4‐dihydroisoquinoline dichlorophosphate

intermediate: 2‐
Acetyl
‐6,7‐
dimethoxy
‐1‐
methylene
‐1,2,3,4‐
tetrahydroisoquinoline

intermediate: 2‐(2‐
Acetamidoethyl
)‐4,5‐
dimethoxyacetophenone

product: R
1
 = OCH
3
, R
2
 = R
3
 = H

product: R
1
, R
2
 = OCH
2
O, R
3
 = H

product: R
1
 = R
2
 = R
3
 = OCH
3
3‐Alkylated and 3‐Acylated Indoles from a Common Precursor: 3‐Benzylindole and 3‐Benzoylindole
Authors: Stütz P. , Stadler P. A.
Published: November 2003

3‐Alkylated and 3‐acylated indoles from a common precursor: 3‐benzylindole and 3‐benzoylindole

intermediate: 2‐phenyl‐1,3‐dithiane

intermediate: 2‐methylthio‐2‐phenyl‐1,3‐dithiane

intermediate: 3‐(2‐phenyl‐1,3‐dithian‐2‐yl)‐1
H
‐indole

product: 3‐benzoylindole

product: 3‐benzylindole
Carboxylation of Aromatic Compounds: Ferrocenecarboxylic Acid
Authors: Reeves Perry C.
Published: November 2003

Carboxylation of aromatic compounds: ferrocenecarboxylic acid

intermediate: (2‐chlorobenzoyl)ferrocene

product: ferrocenecarboxylic acid

product: carboxycyclopentadienyltricarbonylmanganese

product: biphenyl‐4‐carboxylic acid

product: 3,4‐dimethylbenzoic acid

product: 2,4,6‐trimethylbenzoic acid

product: 3,4‐dimethoxybenzoic acid

product: 2,4‐dimethoxybenzoic acid
Chain Elongation of Alkenes
via gem
‐Dihalocyclopropanes: 2‐Bromo‐3,3‐diphenyl‐2‐propen‐1‐yl Acetate
Authors: Sandler Stanely R.
Published: November 2003

Chain elongation of alkenes
via gem
‐dihalocyclopropanes: 2‐bromo‐3,3‐diphenyl‐2‐propen‐1‐yl acetate

product: 2‐Bromo‐3,3‐diphenyl‐2‐propen‐1‐yl acetate

intermediate: 17.6 g. (0.0500 mole) of 1,1‐dibromo‐2,2‐diphenylcyclopropane
Conversion of Nitro to Carbonyl by Ozonolysis of Nitronates: 2,5‐Heptanedione
Authors: McMurry John E. , Melton Jack
Published: November 2003

Conversion of nitro to carbonyl by ozonolysis of nitronates: 2,5‐heptanedione

intermediate: 5‐nitroheptan‐2‐one

product: 2,5‐heptanedione
Demethylation of Methyl Aryl Ethers: 4‐Ethoxy‐3‐Hydroxybenzaldehyde
Authors: Ireland Robert E. , Walba David M.
Published: November 2003

Demethylation of methyl aryl ethers: 4‐ethoxy‐3‐hydroxybenzaldehyde

reactant: 5.0 g. (0.028 mole) of 4‐ethoxy‐3‐methoxybenzaldehyde

reactant: 5.0 ml. (0.029 mole) of diphenylphosphine

intermediate: 5.0 g. (0.022 mole) of 4‐ethoxy‐3‐methoxybenzaldehyde ethylene acetal

product: 4‐hydroxy‐3‐ethoxybenzaldehyde
Indoles from Anilines: Ethyl 2‐Methylindole‐5‐Carboxylate
Authors: Gassman P. G. , van Bergen T. J.
Published: November 2003

Indoles from anilines: ethyl 2‐methylindole‐5‐carboxylate

intermediate: methylthio‐2‐propanone

intermediate: ethyl 2‐methyl‐3‐methylthioindole‐5‐carboxylate

product: ethyl 2‐methylindole‐5‐carboxylate
Peptide Syntheses UsingN‐Ethyl‐5‐Phenylisoxazolium‐3′‐Sulfonate: Carbobenzoxy‐L‐Asparaginyl‐L‐Leucine Methyl Ester andN‐Carbobenzoxy‐3‐Hydroxy‐L‐Prolylglycylglycine Ethyl Ester
Authors: Woodward R. B. , Olofson R. A.
Published: November 2003

Peptide syntheses usingN‐ethyl‐5‐phenylisoxazolium‐3′‐sulfonate: carbobenzoxy‐L‐asparaginyl‐L‐leucine methyl ester andN‐carbobenzoxy‐3‐hydroxy‐L‐prolylglycylglycine ethyl ester

reactant: 2.024 g. (0.00800 mole) ofN‐ethyl‐5‐phenylisoxazolium‐3′‐sulfonate

reactant: 810 mg. (0.00802 mole) of triethylamine

reactant: 1.452 g. (0.00800 mole) ofL‐leucine methyl ester hydrochloride

product: carbobenzyloxy‐L‐asparaginyl‐L‐leucine methyl ester

reactant: 796 mg. (0.00300 mole) ofN‐carbobenzyloxy‐3‐hydroxy‐L‐proline

reactant: 590 mg. (0.00300 mole) of glycylglycine ethyl ester hydrochloride

product:N‐carbobenzyloxy‐3‐hydroxy‐L‐prolylglycylglycine ethyl ester

solvent: petroleum ether

product: Z‐(Nε‐Z)‐Lys·Gly‐OEt[Glycine,N‐[N2,N6‐bis‐[(phenylmethoxy)carbonyl]‐L‐lysyl]‐, ethyl ester]

product: Z‐Phe·Gly‐OEt[Glycine,N‐[N‐[(phenylmethoxy)‐carbonyl]‐L‐phenylalanyl]‐, ethyl ester]

product: Z‐Phe·Leu‐OMe[L‐Leucine,N‐[N‐[(phenylmethoxy)‐carbonyl]‐L‐phenylalanyl]‐, methyl ester]

product: Z‐Met·Gly·Gly‐OEt[Glycine,N‐[N‐[N‐(phenylmethoxy)carbonyl]‐L‐methionyl]glycyl‐, ethyl ester]

product: Phth‐Gly·Gly‐OEt[Glycine,N‐[(1,3‐dihydro‐1,3‐dioxo‐2H‐isoindol‐2‐yl)acetyl]‐, ethyl ester]

product: Z‐Gly·Gly·Tyr‐OMe[L‐Tyrosine,N‐[N‐[N‐[(phenylmethoxy)carbonyl]glycyl]glycyl]‐, methyl ester]

product: Z‐Gly·DL‐Phe·Gly‐OEt[Glycine,N‐[N‐N‐[(phenylmethoxy)carbonyl]glycyl‐DL‐phenelalanyl]‐, ethyl ester]

product: Z‐Gly·Gly·Gly‐OEt[Glycine,N‐[N‐[N‐[(phenylmethoxy)carbonyl]glycyl]glycyl]‐, ethyl ester]

product: Z‐Gly‐NHBz[Carbamic acid, [2‐oxo‐2‐[(phenylmethyl)amino]ethyl]‐, phenylmethyl ester]

product: Z‐Asp·Gly‐OEt [Glycine,N‐[N2‐[(phenylmethoxy)carbonyl]‐L‐asparaginyl]‐, ethyl ester]

product: Z‐Gln·Val‐OMe[L‐Valine,N‐[N2‐[(phenylmethoxy)carbonyl]‐Lglutaminyl]‐, methyl ester]

product: Z‐Gln·Tyr‐OMe[L‐Tyrosine,N‐[N2‐[(phenylmethoxy)carbonyl]‐L‐glutaminyl]‐, methyl ester]
Polymeric Carbodiimide.
M
offat Oxidation: 4‐
tert
‐Butylcyclohexanone
Authors: Weinshenker Ned M. , Shen Chah M. , Wong Jack Y.
Published: November 2003

Polymeric carbodiimide. Moffat oxidation: 4‐
tert
‐butylcyclohexanone

product: 4‐
tert
‐butylcyclohexanone
Trifluoroacetylation of Amines and Amino Acids under Neutral, Mild Conditions:
N
‐Trifluoroacetanilide and
N
‐Trifluoroacetyl‐L‐Tyrosine
Authors: Panetta C. A.
Published: November 2003

Trifluoroacetylation of amines and amino acids under neutral, mild conditions:
N
‐trifluoroacetanilide and
N
‐trifluoroacetyl‐L‐tyrosine

reactant: 21.5 g. (0.0998 mole) of 1,1,1‐trichloro‐3,3,3‐trifluoroacetone

product:
N
‐trifluoroacetanilide

product:
N
‐trifluoroacetyl‐
L
‐tyrosine

reactant: 35.0 g. (0.192 mole) of chloropentafluoroacetone (b.p. 7.8°; available from PCR, Inc., or Allied Chemical Corp.)

product: TFA‐Aniline

product: TFA‐
L
‐Valine

product: TFA‐
DL
‐Phenylalanine

product: TFA‐
L
‐Phenylalanine

product: TFA‐
L
‐Leucine

product: TFA‐
L
‐Tyrosine

product: TFA‐
L
‐Proline

product: TFA‐
DL
‐Alanine

product: TFA‐Glycylglycine

product: TFA‐
L
‐Prolyglycine, ethyl ester

product: TFA‐
L
‐Asparagine

product: TFA‐Dehydroabietylamine
2‐Adamantanecarbonitrile
Authors: Oldenziel O. H. , Wildeman J. , van Leusen A. M.
Published: November 2003

2‐adamantanecarbonitrile

solvent: petroleum ether

product: 2‐adamantanecarbonitrile

reactant:
p
‐tolylsulfonylmethyl isocyanide

product: 2‐adamantanecarboxylic acid
Aldehydes from Olefins: Cyclohexanecarboxaldehyde
Authors: Pino P. , Botteghi C.
Published: November 2003

Aldehydes from olefins: cyclohexanecarboxaldehyde

product: cyclohexanecarboxaldehyde
Bis[2,2,2‐trifluoro‐1‐phenyl‐1‐(trifluoromethyl) Ethoxy] Diphenyl Sulfurane
Authors: Martin J. C. , Arhart R. J. , Franz J. A. , Perozzi E. F. , Kaplan L. J.
Published: November 2003

Bis[2,2,2‐trifluoro‐1‐phenyl‐1‐(trifluoromethyl) ethoxy] diphenyl sulfurane

reactant: 100.0 g. (0.4098 mole) of 1,1,1,3,3,3‐hexafluoro‐2‐phenyl‐2‐propanol

intermediate: potassium 1,1,1,3,3,3‐hexafluoro‐2‐phenyl‐2‐propanolate

product:
Bis
[2,2,2‐
trifluoro
‐1‐
phenyl
‐1‐(
trifluoromethyl
)
ethoxy
]
diphenyl sulfurane
(
Z
)‐4‐Chloro‐4‐Hexenyl Trifluoroacetate
Authors: Peterson P. E. , Dunham M.
Published: November 2003

(
Z
)‐4‐chloro‐4‐hexenyl trifluoroacetate

reactant: 35.3 g. (50.0 ml., 0.882 mole) of precondensed propyne

reactant: 153.5 g. (0.975 mole) of 1‐bromo‐3‐chloropropane

intermediate: 6‐chloro‐2‐hexyne

product: 4‐chloro‐4‐hexenyl trifluoroacetate
Cyclopropenone
Authors: Breslow R. , Pecoraro J. , Sugimoto T.
Published: November 2003

Cyclopropenone

intermediate: 1‐bromo‐3‐chloro‐2,2‐dimethoxypropane (21.7 g., 0.100 mole)

intermediate: 3,3‐dimethoxycyclopropene

product: cyclopropenone
4‐Nitrobenzyl Fluoride
Authors: Middleton W. J. , Bingham E. M.
Published: November 2003

4‐Nitrobenzyl fluoride

product: 4‐nitrobenzyl fluoride
2,2,7,7,12,12,17,17‐Octamethyl‐21,22,23,24‐tetraoxaperhydroquaterene
Authors: Chastrette Maurice , Chastrette Francine , Sabadie Jean
Published: November 2003

2,2,7,7,12,12,17,17‐octamethyl‐21,22,23,24‐tetraoxaperhydroquaterene

intermediate: 2,2,7,7,12,12,17,17‐
Octamethyl
‐21,22,23,24‐
tetraoxaquaterene.

reactant: 27.2 g. (0.400 mole) of freshly distilled furan

catalyst: 57.3 g. (0.200 mole) of the lithium perchlorate–1,2‐dimethoxyethane complex

product: 2,2,7,7,12,12,17,17‐
Octamethyl
‐21,22,23,24‐
tetraoxaperhydroquaterene.
(Pentafluorophenyl)Acetonitrile
Authors: Filler Robert , Woods Sarah M.
Published: November 2003

(Pentafluorophenyl)Acetonitrile

intermediate: ethyl cyano(pentafluorophenyl)acetate

product:
(Pentafluorophenyl)acetonitrile

reactant: Hexafluorobenzene was purchased from PCR, Inc., Gainesville, Florida

product: 2,3‐bis(pentafluorophenyl)propionitrile

product: bis(pentafluorophenyl)acetonitrile

product: 2‐(pentafluorophenyl)ethylamine hydrochloride

product: 4,5,6,7‐tetrafluoroindoline
Sulfonyl Cyanides: Methanesulfonyl Cyanide
Authors: Vrijland M. S. A.
Published: November 2003

Sulfonyl cyanides: methanesulfonyl cyanide

product: methanesulfonyl cyanide
3,3,6,6‐Tetramethoxy‐1,4‐Cyclohexadiene
Authors: Margaretha Paul , Tissot Paul
Published: November 2003

3,3,6,6‐Tetramethoxy‐1,4‐cyclohexadiene

product: 3,3,6,6‐tetramethoxy‐1,4‐cyclohexadiene
p
‐Tolylsulfonylmethyl Isocyanide
Authors: Hoogenboom B. E. , Oldenziel O. H. , van Leusen A. M.
Published: November 2003

p
‐Tolylsulfonylmethyl isocyanide

intermediate:
N
‐(
p
‐tolylsulfonylmethyl)formamide

solvent: One liter of petroleum ether

product:
p
‐tolylsulfonylmethyl isocyanide
Arene Oxide Synthesis: Phenanthrene‐9,10‐Oxide
Authors: Cortez Cecilia , Harvey Ronald G.
Published: November 2003

ARENE OXIDE SYNTHESIS: PHENANTHRENE‐9,10‐OXIDE

intermediate: trans‐9,10‐
Dihydro
‐9,10‐
phenanthrenediol
(1)

product:
Phenanthrene
‐9,10‐
oxide
(2)
Catalytic Osmium Tetroxide Oxidation of Olefins:cis‐1,2‐Cyclohexanediol
Authors: VanRheenen V. , Cha D. Y. , Hartley W. M.
Published: November 2003

Catalytic osmium tetroxide oxidation of olefins:cis‐1,2‐cyclohexanediol

product: cis‐1,2‐Cyclohexanediol(2)

intermediate:N‐MethylmorpholineN‐oxide (1) can also be purchased from Eastman Organic Chemicals or Fluka A G
Copper Catalyzed Arylation of β‐Dicarbonyl Compounds: 2‐(1‐Acetyl‐2‐Oxopropyl)Benzoic Acid
Authors: Bruggink Alle , Ray Stephen J. , McKillop Alexander
Published: November 2003

Copper catalyzed arylation of β‐dicarbonyl compounds: 2‐(1‐acetyl‐2‐oxopropyl)benzoic acid

reactant: Commercial 2‐bromobenzoic acid, purchased from Aldrich Chemical Company, Inc.

product: 2‐(1‐Acetyl‐2‐oxopropyl)benzoic acid

byproduct: 2‐ethoxybenzoic acid

reactant: 2‐bromobenzoic acid
γ‐Ketoesters from AldehydesViaDiethyl Acylsuccinates: Ethyl 4‐Oxohexanoate
Authors: Wehrli Pius A. , Chu Vera
Published: November 2003

γ‐Ketoesters from aldehydesviadiethyl acylsuccinates: ethyl 4‐oxohexanoate

intermediate:Diethyl propionylsuccinate

product: ethyl 4‐oxohexanoate
γ‐Ketoesters to prepare Cyclic Diketones: 2‐Methyl‐1,3‐Cyclopentanedione
Authors: Hengartner U. , Chu Vera
Published: November 2003

γ‐Ketoesters to prepare cyclic diketones: 2‐methyl‐1,3‐cyclopentanedione

solvent: 1.4 l. of xylene

product: 2‐methyl‐1,3‐cyclopentanedione
Macrocyclic Polyamines: 1,4,7,10,13,16‐Hexaäzacycloöctadecane
Authors: Atkins T. J. , Richman J. E. , Oettle W. F.
Published: November 2003

Macrocyclic polyamines: 1,4,7,10,13,16‐hexaäzacycloöctadecane

intermediate: N,N′,N″‐
Tris
(p‐
tolylsulfonyl
)
diethylenetriamine
(1)

intermediate: N,N′,N″‐
Tris
(p‐
tolysulfonyl
)
diethylenetriamine
‐N,N″‐
disodium salt
(2)

intermediate: 3,6,9‐
Tris
(p‐
tolylsulfonyl
)‐3,6,9‐
triazaundecane
‐1,11‐
diol
(3)

intermediate: 3,6,9‐
Tris
(p‐
tolylsulfonyl
)‐3,6,9‐
triazaundecane
‐1,11‐
dimethanesulfonate
(4)

intermediate: 1,4,7,10,13,16‐
Hexakis
(p‐
tolylsulfonyl
)‐1,4,7,10,13,16‐
hexaäzacycloöctadecane
(5)

product: 1,4,7,10,13,16‐hexaäzacycloöctadecane (6)
Macrolides from Cyclization of ω‐Bromocarboxylic Acids: 11‐Hydroxyundecanoic Lactone
Authors: Galli C. , Mandolini L.
Published: November 2003

Macrolides from cyclization of ω‐bromocarboxylic acids: 11‐hydroxyundecanoic lactone

product: 11‐hydroxyundecanoic lactone

product: 1,13‐dioxacyclotetracosane‐2,14‐dione

product: 15‐hydroxypentadecanoic lactone

product: 17‐hydroxyheptadecanoic lactone
Nitriles from Ketones: Cyclohexanecarbonitrile
Authors: Wender P. A. , Eissenstat M. A. , Sapuppo N. , Ziegler F. E.
Published: November 2003

Nitriles from ketones: cyclohexanecarbonitrile

intermediate:
Methyl
2‐(1‐
cyanocyclohexyl)hydrazine carboxylate
(1)

intermediate:
Methyl
2‐(1‐
cyancyclohexyl)diaxenecarboxylate
(2)

product: cyclohexanecarbonitrile (3)
Nucleophilic α‐
sec
‐Aminoalkylation: 2‐(Diphenylhydroxymethyl)pyrrolidine
Authors: Enders D. , Pieter R. , Renger B. , Seebach D.
Published: November 2003

Nucleophilic α‐
sec
‐aminoalkylation: 2‐(Diphenylhydroxymethyl)pyrrolidine

product: 2‐(Diphenylhydroxymethyl)pyrrolidine

reactant: 4 g. (0.05 mole) of ethyl nitrite

reactant: 2.35 g. (0.0331 mole) of pyrrolidine

reactant: 3.44 g. (4.76 ml., 0.0341 mole) of diisopropylamine

reactant: 5.46 g. (0.0300 mole) of benzophenone in 12 ml. of tetrahydrofuran
Sulfide Synthesis: Benzyl Sulfide
Authors: Harpp David N. , Smith Roger A.
Published: November 2003

Sulfide synthesis: Benzyl sulfide

reactant: 3.92 g. (0.0240 mole) of freshly‐distilled hexamethylphosphorous triamide

product: benzyl sulfide
3‐Trimethylsilyl‐3‐Buten‐2‐One as
M
ichael Acceptor for Conjugate Addition‐Annelation:
cis
‐4,4
a
,5,6,7,8‐Hexahydro‐4
a
,5‐Dimethyl‐2(3
H
)‐Naphthalenone
Authors: Boeckman Robert K. , Blum David M. , Ganem Bruce
Published: November 2003

3‐Trimethylsilyl‐3‐buten‐2‐one as michael acceptor for conjugate addition‐annelation:
cis
‐4,4
a
,5,6,7,8‐hexahydro‐4
a
,5‐dimethyl‐2(3
H
)‐naphthalenone

product:
cis
‐4,4
a
,5,6,7,8‐HEXAHYDRO‐4
a
,5‐DIMETHYL‐2(3
H
)‐NAPHTHALENONE
Conjugate Reduction of α,β‐Unsaturated
p
‐Toluenesulfonylhydrazones to Alkenes with Catecholborane: 5β‐Cholest‐3‐Ene
Authors: Kabalka George W. , Hutchins Robert , Natale Nicholas R. , Yang Dominic T. C. , Broach Vicky
Published: November 2003

Conjugate reduction of α,β‐unsaturated
p
‐toluenesulfonylhydrazones to alkenes with catecholborane: 5β‐cholest‐3‐ene

intermediate: cholest‐4‐en‐3‐one
p
‐toluenesulfonylhydrazone

product: 5β‐cholest‐3‐ene

product: C
6
H
5
CH
2
CHCHCH
3

product: C
6
H
5
CH
2
CHCH
2

product: (CH
3
)
2
CHCHCHCH
3

product: CH
3
(CH
2
)
3
CHCCHCH
3

product: CH
3
CHCCHC
6
H
5

byproduct: 5β‐cholestane

byproduct: 5α‐cholestane

byproduct: 5α‐cholest‐3‐ene
α,β‐Dehydrogenation of β‐Dicarbonyl Compounds by Selenoxide Elimination: 2‐Acetyl‐2‐Cyclohexen‐1‐One
Authors: Renga James M. , Reich Hans J.
Published: November 2003

α,β‐dehydrogenation of β‐dicarbonyl compounds by selenoxide elimination: 2‐acetyl‐2‐cyclohexen‐1‐one

intermediate: 2‐acetyl‐2‐phenylselenocyclohexanone

product: 2‐acetyl‐2‐cyclohexen‐1‐one

reactant: benzeneseleninic acid
Highly Reactive Magnesium for the Preparation of
G
rignard Reagents: 1‐Norbornanecarboxylic Acid
Authors: Rieke Reuben D. , Bales Stephen E. , Hudnall Phillip M. , Burns Timothy P. , Poindexter Graham S.
Published: November 2003

Highly reactive magnesium for the preparation of Grignard reagents: 1‐norbornanecarboxylic acid

intermediate: 2,2‐dichloronorbornane

intermediate: 1‐chloronorbornane

product: 1‐norbornanecarboxylic acid
NucleophilicAcylation with Disodium Tetracarbonylferrate: Methyl 7‐Oxoheptanoate and Methyl 7‐Oxoöctanoate
Authors: Finke Richard G. , Sorrell Thomas N.
Published: November 2003

Nucleophilic Acylation with Disodium Tetracarbonylferrate: Methyl 7‐Oxoheptanoate and Methyl 7‐Oxoöctanoate

intermediate: Disodium tetracarbonylferrate sesquidioxanate

product:
Methyl
7‐
oxoheptanoate

product:
Methyl
7‐
oxo
ö
ctanoate

reactant: Methyl 6‐bromohexanoate
Pentafluorophenylcopper Tetramer, A Reagent for Synthesis of Fluorinated Aromatic Compounds
Authors: Cairncross Allan , Sheppard William A. , Wonchoba Edward
Published: November 2003

Pentafluorophenylcopper tetramer, a reagent for synthesis of fluorinated aromatic compounds

intermediate: bis(pentafluorophenylcopper)dioxane complex

product: pentafluorophenylcopper tetramer

solvent: dioxane

product: C6F5Cu·benzonitrile

product: C6F5Cu·tributylamine

product: (C6F5Cu)2·dioxane

product: C6F5Cu·quinoline

product: (C6F5Cu)2·1,5‐cycloöctadiene

product: C6F5Cu·dimethylacetylene

product: (C6F5Cu)2·butadiene

product: C6F5Cu·tetraethylammonium cyanide

product: C6F5H

product: C6F5‐C6F5

product: C6F5Br(4) + C6F5‐C6F5

product: C6F5‐C6F5

product: CH3‐C6F5

product: C6H5CH2C6F5

product: 1‐pentafluorophenylbicyclo[2.2.2]octane

product: (C2H5O2)CCH2C6F5

product: C6F5‐C6H5

product: 3‐FC6H4‐C6F5

product: O2NC6H4C6F5meta

product: 4‐(CH3)2NC6H4C6F5

product: 4‐C2H5O2CC6H4C6F5

product: C6F5CFCF2

product: C6F5CCC6F5

product: C6H5‐C6F5

product: (C2H5)3SiCCC6F5

product:(Pentafluorophenyl)benzene

product: 1‐(Pentafluorophenyl)adamantane
Reagents for Synthesis of Organoselenium Compounds: Diphenyl Diselenide and Benzeneselenenyl Chloride
Authors: Reich Hans J. , Cohen Martin L. , Clark Peter S.
Published: November 2003

Reagents for synthesis of organoselenium compounds: diphenyl diselenide and benzeneselenenyl chloride

product: diphenyl diselenide

product: benzeneselenenyl chloride

product: C
6
H
5
SeBr

product: C
6
H
5
SeNa

product: C
6
H
5
SeH
Tertiary Alcohols from Hydrocarbons by Ozonation on Silica Gel: 1‐Adamantanol
Authors: Cohen Zvi , Varkony Haim , Keinan Ehud , Mazur Yehuda
Published: November 2003

Tertiary alcohols from hydrocarbons by ozonation on silica gel: 1‐adamantanol

product: adamantanol

product: 1,3‐adamantanediol
Thiol Protection with the Acetamidomethyl Group:
S
‐Acetamidomethyl‐
L
‐Cysteine Hydrochloride
Authors: Milkowski John D. , Veber Daniel F. , Hirschmann Ralph
Published: November 2003

Thiol protection with the acetamidomethyl group:
S
‐acetamidomethyl‐
L
‐cysteine hydrochloride

intermediate:
N
‐(hydroxymethyl)acetamide

product:
S
‐acetamidomethyl‐
L
‐cysteine hydrochloride

byproduct:
S
‐acetamidomethyl‐
L
‐cysteine monohydrate
Anodic Oxidation of Acids: Dimethyl Decanedioate
Authors: White D. A.
Published: November 2003

Anodic oxidation of acids: Dimethyl decanedioate

byproduct: dimethyl hexanedioate

product: dimethyl decanedioate
Cyclopropanecarboxaldehyde
Authors: Barnier J. P. , Champion J. , Conia J. M.
Published: November 2003

Cyclopropanecarboxaldehyde

intermediate:
cis
‐ and
trans
‐1,2‐cyclobutanediol

product: cyclopropanecarboxaldehyde
Homoconjugate Addition of Nucleophiles to Cyclopropane‐1,1‐Dicarboxylate Derivatives: 2‐Oxo‐1‐Phenyl‐3‐Pyrrolidinecarboxylic Acid
Authors: Singh Rajendra K. , Danishefsky Samuel
Published: November 2003

Homoconjugate addition of nucleophiles to cyclopropane‐1,1‐dicarboxylate derivatives: 2‐Oxo‐1‐phenyl‐3‐pyrrolidinecarboxylic acid

intermediate: 6,6‐Dimethyl‐5,7‐dioxaspiro[2.5]octane‐4,8‐dione

product: 2‐Oxo‐1‐phenyl‐3‐pyrrolidinecarboxylic acid (3)

intermediate: cyclopropane‐1,1‐dicarboxylic acid

intermediate: 1‐cyanocyclopropanecarboxylic acid

intermediate: 1‐acetylcyclopropanecarboxylic acid
Indirect Electrolysis: Tetramethyl 1,1,2,2‐ethanetetracarboxylate
Authors: White Donald A.
Published: November 2003

Indirect electrolysis: Tetramethyl 1,1,2,2‐ethanetetracarboxylate

product: tetramethyl ethenetetracarboxylate
Methylene Ketones and Aldehydes by Simple, Direct Methylene Transfer: 2‐Methylene‐1‐Oxo‐1,2,3,4‐Tetrahydronaphthalene
Authors: Gras Jean‐Louis
Published: November 2003

Methylene ketones and aldehydes by simple, direct methylene transfer: 2‐methylene‐1‐oxo‐1,2,3,4‐tetrahydronaphthalene

product: 2‐METHYLENE‐1‐OXO‐1,2,3,4‐TETRAHYDRONAPHTHALENE

reactant: 16.57 g (0.075 mol) of
N
‐methylanilinium trifluoroacetate
2‐Phenyl‐2‐Adamantanamine Hydrochloride
Authors: Kalir Asher , Balderman David
Published: November 2003

2‐Phenyl‐2‐adamantanamine hydrochloride

reactant: 22.8 g (0.1 mol) of 2‐phenyl‐2‐adamantanol

intermediate: 24 g (0.095 mol) of the crude 2‐azido‐2‐phenyladamantane

product: 2‐phenyl‐2‐adamantanamine hydrochloride

product: 2‐butyl‐2‐adamantanamine hydrochloride
Trimethylsilyl Cyanide: Cyanosilation of
p
‐Benzoquinone
Authors: Livinghouse Tom
Published: November 2003

Trimethylsilyl cyanide: Cyanosilation of
p
‐benzoquinone

intermediate: trimethylsilyl cyanide

product:
p
‐Benzoquinone monotrimethylsilyl cyanohydrin
Oxidation of 5‐Aminotetrazoles: Benzyl Isocyanide
Authors: Höfle Gerhard , Lange Bernd
Published: November 2003

Oxidation of 5‐aminotetrazoles: benzyl isocyanide

product: benzyl isocyanide

product: C6H5
Chiral Media for Asymmetric Solvent Inductions. (
S,S
)‐( + )‐1,4‐Bis(dimethylamino)‐2,3‐dimethoxybutane from (
R,R
)‐( + )‐Diethyl Tartrate
Authors: Seebach Dieter , Kalinowski Hans‐Otto , Langer Werner , Crass Gerhard , Wilka Eva‐Maria
Published: November 2003

Chiral media for asymmetric solvent inductions. (
S,S
)‐( + )‐1,4‐Bis(dimethylamino)‐2,3‐dimethoxybutane from (
R,R
)‐( + )‐diethyl tartrate

intermediate: (R,R)‐( + )‐N,N,N′,N′‐Tetramethyltartaric acid diamide

reactant: 450 mL (7 mol) of liquid, anhydrous, cold (− 78°C) dimethylamine

intermediate: (R,R)‐( + )‐2,3‐Dimethoxy‐N,N,N′,N′‐tetramethylsuccinic acid diamide

product: (S,S)‐( + )‐1,4‐Bis (dimethylamino)‐2,3‐dimethoxybutane (DDB)

reactant: (R,R)‐( + )‐diethyl tartrate

reactant: (R,R)‐( + )‐tartaric acid (Firma Benckiser, D‐Ludwigshafen, or Firma Boehringer, D‐Ingelheim)
Cyanic Acid Esters from Phenols: Phenyl Cyanate
Authors: Martin D. , Bauer M.
Published: November 2003

Cyanic acid esters from phenols: phenyl cyanate

product: phenyl cyanate

product: 2‐CH3C6H4OCN

product: 4‐CH3C6H4OCN

product: 4‐CH3OC6H4OCN

product: 2‐ClC6H4OCN

product: 4‐ClC6H4OCN

product: 2‐CH3OCOC6H4OCN

product: 2‐Naphthyl‐OCN

product: 4‐NCOC6H4OCN

product: CCl3CH2OCN

product: CF3CH2OCN
Alkylation of the Anion from Birch Reduction of
o
‐Anisic Acid: 2‐Heptyl‐2‐Cyclohexenone
Authors: Taber D. F. , Gunn B. P. , Chiu I‐Ching
Published: November 2003

Alkylation of the anion from birch reduction of
o
‐anisic acid: 2‐heptyl‐2‐cyclohexenone

product: 2‐heptyl‐2‐cyclohexenone