bluuebunny/crossref_metadata_2025 huggingface dataset:
Acetone Hydrazone
Authors: Day A. C. , Whiting M. C.
Published: November 2003

Acetone hydrazone

intermediate: acetone azine
Bis(trifluoromethyl)diazomethane
Authors: Middleton W. J. , Gale D. M.
Published: November 2003

Bis(trifluoromethyl)diazomethane

reactant: 82.5 g. (0.500 mole) of hexafluoroacetone imine

intermediate: hexafluoroacetone hydrazone

product: bis(trifluoromethyl)diazomethane
Cyclobutadieneiron Tricarbonyl
Authors: Pettit R. , Henery J.
Published: November 2003

Cyclobutadieneiron tricarbonyl

byproduct: iron pentacarbonyl

product: cyclobutadieneiron tricarbonyl
2‐Diazopropane
Authors: Andrews S. D. , Day A. C. , Raymond P. , Whiting M. C.
Published: November 2003

2‐Diazopropane

product: 2‐diazopropane
1‐Nitrocycloöctene
Authors: Seifert Wolfgang K.
Published: November 2003

1‐Nitrocycloöctene

product: 1‐nitrocycloöctene

product: 1‐nitro‐1‐octadecene
Aldehydes from Acid Chlorides by Reduction of Ester‐Mesylates with Sodium Borohydride: Cyclobutanecarboxaldehyde
Authors: Johnson M. Ross , Rickborn Bruce
Published: November 2003

Aldehydes from acid chlorides by reduction of ester‐mesylates with sodium borohydride: cyclobutanecarboxaldehyde

reactant: 37 g. (0.52 mole) of
trans
‐2‐butene oxide

intermediate:
erythro
‐2,3‐butanediol monomesylate

intermediate:
erythro
‐3‐methanesulfonyloxy‐2‐butyl cyclobutanecarboxylate

intermediate: 2‐cyclobutyl‐
cis
‐4‐
trans
‐5‐dimethyl‐1,3‐dioxolane

product: cyclobutanecarboxaldehyde
2‐Diazocycloalkanones: 2‐Diazocyclohexanone
Authors: Regitz Manfred , Rüter Jörn , Liedhegener Annemarie
Published: November 2003

2‐Diazocycloalkanones: 2‐Diazocyclohexanone

reactant: 106 g. (1.05 moles) of triethylamine

product: 2‐diazocyclohexanone
β‐Diketones from Methyl Alkyl Ketones: 3‐
n
‐Butyl‐2,4‐Pentanedione
Authors: Mao Chung‐Ling , Hauser Charles R.
Published: November 2003

β‐Diketones from methyl alkyl ketones: 3‐
n
‐butyl‐2,4‐pentanedione

reactant: 28.6 g. (0.251 mole) of 2‐heptanone

reactant: 51.0 g. (0.500 mole) of acetic anhydride

solvent: 100‐ml. portions of petroleum ether

product: 3‐
n
‐butyl‐2,4‐pentanedione

product: 3‐methyl‐2,4‐pentanedione

product: 3‐ethyl‐2,4‐pentanedione

product: 3‐phenyl‐2,4‐pentanedione

product: 3,3‐dimethyl‐2,4‐pentanedione

product: 2‐acetylcyclohexanone

product: 2‐acetylcyclopentanone

product: 3‐methyl‐2,4‐hexanedione

product: 1,3‐diphenyl‐2,4‐pentanedione

product: benzoylacetone
Esterification of Hindered Alcohols:
tert
‐Butyl
p
‐Toluate
Authors: Crowther G. P. , Kaiser E. M. , Woodruff R. A. , Hauser C. R.
Published: November 2003

Esterification of hindered alcohols:
tert
‐butyl
p
‐toluate

reactant: 5.42 g. (0.0351 mole) of
p
‐toluoyl chloride

product:
tert
‐butyl
p
‐toluate

product:
tert
‐butyl phenylacetate

product: triethylcarbinol ester of
p
‐toluic acid

product: 2,2‐diphenylethanol ester of benzoic acid

product: C
6
H
5
CH
2
CO
2
C(CH
3
)
3

product: C
6
H
5
CO
2
CH
2
CH(C
6
H
5
)
2

product: C
6
H
5
CO
2
C(CH
3
)
3

product: C
6
H
5
CO
2
CCH
3
(C
2
H
5
)
2

product: C
6
H
5
CO
2
C(C
2
H
5
)
3

product: C
6
H
5
CO
2
CH
2
(t‐C
4
H
9
)

product: (CH
3
)
3
CCO
2
C(CH
3
)
3

product: (CH
3
)
3
CCO
2
C(C
2
H
5
)

product: (i‐C
3
H
7
)
2
CHCO
2
C(C
2
H
5
)
3

product: C
6
H
5
CHCHCO
2
C(CH
3
)
3

product: (tC4H9)CH
2
CO
2
C(C
2
H
5
)
3

product: C
6
H
5
CH
2
CH
2
CO
2
C(CH
3
)
3

product: (tC
4
H
9
)
2
CHCO
2
C(C
2
H
5
)
3
6‐Methoxy‐β‐Tetralone
Authors: Sims James J. , Selman L. H. , Cadogan M.
Published: November 2003

6‐Methoxy‐β‐tetralone

reactant: 36.9 g. (0.200 mole) of (4‐methoxyphenyl)acetyl chloride

product: 6‐methoxy‐β‐tetralone

solvent: Matheson, Coleman and Bell dichloromethane

reactant: (4‐methoxyphenyl)acetic acid (Aldrich Chemical Company, Inc., m.p. 85–86.5°)
Metalation of 2‐Methylpyridine Derivatives: Ethyl 6‐Methylpyridine‐2‐Acetate
Authors: Kofron William G. , Baclawski Leona M.
Published: November 2003

Metalation of 2‐Methylpyridine Derivatives: Ethyl 6‐Methylpyridine‐2‐Acetate

reactant: 32.1 g. (0.300 mole) of 2,6‐lutidine

product: ethyl 6‐methylpyridine‐2‐acetate
Oxidation with the Nitrosodisulfonate Radical.
I
. Preparation and use of Disodium Nitrosodisulfonate: Trimethyl‐
p
‐Benzoquinone
Authors: Wehrli Pius A. , Pigott Foster
Published: November 2003

Oxidation with the nitrosodisulfonate radical. I. preparation and use of disodium nitrosodisulfonate: trimethyl‐
p
‐benzoquinone

product:
Disodium nitrosodisulfonate

product:
Trimethyl
‐p‐
benzoquinone

reactant: 2,3,6‐trimethylphenol, purchased from Aldrich Chemical Company, Inc.
Use of Dipotassium Nitrosodisulfonate (Fremy's Salt): 4,5‐Dimethyl‐
o
‐Benzoquinone
Authors: Teuber H.‐J.
Published: November 2003

use of dipotassium nitrosodisulfonate (Fremy's salt): 4,5‐dimethyl‐
o
‐benzoquinone

product: 4,5‐dimethyl‐
o
‐benzoquinone

reactant: 16 g. (0.13 mole) of 3,4‐dimethylphenol
Diethylaluminum Cyanide
Authors: Nagata W. , Yoshioka M.
Published: November 2003

Diethylaluminum cyanide

product: diethylaluminum cyanide
3β‐Acetoxy‐5α‐Cyanocholestan‐7‐One
Authors: Nagata W. , Yoshioka M.
Published: November 2003

3β‐acetoxy‐5α‐cyanocholestan‐7‐one

product: 3β‐Acetoxy‐5α‐cyanocholestan‐7‐one
Reductive Amination with Sodium Cyanoborohydride:
N,N
‐Dimethylcyclohexylamine
Authors: Borch Richard F.
Published: November 2003

Reductive Amination with Sodium Cyanoborohydride:
N,N
‐Dimethylcyclohexylamine

product:
N,N
‐dimethylcyclohexylamine

byproduct: cyclohexanol

product: Cyclohexylamine

product:
N
‐Methylcyclohexylamine

product: α‐Phenylethylamine

product:
N
‐Methylphenethylamine

product:
N
‐Isobutylaniline

product:
N
‐Methylpiperidine
4
H
‐1,4‐Thiazine 1,1‐Dioxide
Authors: Noland Wayland E. , DeMaster Robert D.
Published: November 2003

4
H
‐1,4‐thiazine 1,1‐dioxide

intermediate: cis
and
trans‐2,6‐
Diethoxy
‐1,4‐
oxathiane
4,4‐
dioxide

solvent: 850–950 ml. of boiling heptane

product: 4
H
‐1,4‐thiazine 1,1‐dioxide

solvent: benzene‐petroleum ether

product: 4‐(4‐carboxyphenyl)‐4
H
‐1,4‐thiazine 1,1‐dioxide

product: 2‐nitrophenylacetaldehyde dimethyl acetal

product: bromoacetaldehyde dimethyl acetal

product: malonaldehydic acid diethyl acetal ethyl ester

product: malonaldehyde bis(diethyl acetal)

product: nitroacetaldehyde diethyl acetal
Adamantanone
Authors: Geluk H. W. , Keizer V. G.
Published: November 2003

Adamantanone

product: adamantanone
Azetidine
Authors: Wadsworth Donald H.
Published: November 2003

Azetidine

intermediate:
Ethyl
3‐(1‐
azetidinyl)propionate

intermediate: diethyl 3‐
N
‐(3‐hydroxypropyl)iminodipropionate

product: diethyl 3‐
N
‐(3‐chloropropyl)iminodipropionate

product:
Azetidine
tert‐Butoxycarbonyl‐L‐Proline
Authors: Ragnarsson Ulf , Karlsson Sune M. , Sandberg Bengt E. , Larsson Lars‐Eric
Published: November 2003

tert‐Butoxycarbonyl‐L‐proline

reactant: 115 g. (1.00 mole) of 1,1,3,3‐tetramethylguanidine

product:tert‐butoxycarbonyl‐L‐proline

product: Boc‐Ala

product: Boc‐Ala

product: Boc‐Asn

product: Boc‐Asp

product: Boc‐Cys(Bzl)

product: Boc‐Cys (Bzl)

product: Boc‐Gln

product: Boc‐Glu

product: Boc‐Ile

product: Boc‐Leu

product: Boc‐Met

product: Boc‐Phe

product: Boc‐Phe

product: Boc‐Phe

product: Boc‐Phe

product: Boc‐Phe

product: Boc‐Pro

product: Boc‐Pro

product: Boc‐Pro

product: Boc‐Thr

product: Boc‐Val
4,4‐Dimethyl‐2‐Cyclohexen‐1‐One
Authors: Chan Yihlin , Epstein William W.
Published: November 2003

4,4‐Dimethyl‐2‐cyclohexen‐1‐one

reactant: 61.5 g. (0.853 mole) of isobutyraldehyde

reactant: 60.6 g. (0.852 mole) of pyrrolidine

intermediate: 1‐(2‐Methylpropenyl)pyrrolidine (62.6 g., 0.501 mole)

reactant: 42.1 g. (0.601 mole) of methyl vinyl ketone

product: 4,4‐dimethyl‐2‐cyclohexen‐1‐one
A General Synthesis of 4‐Isoxazolecarboxylic Esters: Ethyl 3‐Ethyl‐5‐Methyl‐4‐Isoxazolecarboxylate
Authors: McMurry John E.
Published: November 2003

A general synthesis of 4‐isoxazolecarboxylic esters: ethyl 3‐ethyl‐5‐methyl‐4‐isoxazolecarboxylate

intermediate: ethyl β‐pyrrolidinocrotonate

product: ethyl 3‐ethyl‐5‐methyl‐4‐isoxazolecarboxylate
Modified Clemmensen Reduction: Cholestane
Authors: Yamamura Shosuke , Toda Masaaki , Hirata Yoshimasa
Published: November 2003

Modified clemmensen reduction: cholestane

product: cholestane

byproduct: 3‐acetoxycholest‐2‐ene

byproduct: cholestan‐3‐one
Oxymercuration‐Reduction: Alcohols from Olefins: 1‐Methylcyclohexanol
Authors: Jerkunica J. M. , Traylor T. G.
Published: November 2003

Oxymercuration‐reduction: alcohols from olefins: 1‐methylcyclohexanol

product: 1‐methylcyclohexanol
Aldehydes from 4,4‐Dimethyl‐2‐Oxazoline and
G
rignard Reagents:
o
‐Anisaldehyde
Authors: Brinkmeyer R. S. , Collington E. W. , Meyers A. I.
Published: November 2003

Aldehydes from 4,4‐dimethyl‐2‐oxazoline and grignard reagents:
o
‐anisaldehyde

intermediate: oxazolidine

product:
o
‐anisaldehyde

reactant: 4,4‐dimethyl‐2‐oxazoline

reactant:
N
,4,4‐Trimethyl‐2‐oxazolinium iodide

byproduct: 5–10%
o
‐bromoanisole

product: C
6
H
5
CHO

product: C
6
H
5
CH
2
CHO

product: C
6
H
5
CHCHCHO

product: C
6
H
5
CCCHO

product: 2‐CH
3
OC
6
H
4
CDO
Alkylations of Aldehydes
via
Reaction of the Magnesioenamine Salt of an Aldehyde: 2,2‐Dimethyl‐3‐Phenylpropionaldehyde
Authors: Stork G. , Dowd S. R.
Published: November 2003

Alkylations of aldehydes
via
reaction of the magnesioenamine salt of an aldehyde: 2,2‐dimethyl‐3‐phenylpropionaldehyde

intermediate:
N
‐(2‐methylpropylidene)‐
tert
‐butylamine

product: 2,2‐dimethyl‐3‐phenylpropionaldehyde

byproduct: 2,4‐dinitrophenylhydrazone
Directed Aldol Condensations:
threo
‐4‐Hydroxy‐3‐Phenyl‐2‐Heptanone
Authors: Auerbach Robert A. , Crumrine David S. , Ellison David L. , House Herbert O.
Published: November 2003

Directed aldol condensations:
threo
‐4‐hydroxy‐3‐phenyl‐2‐heptanone

reactant: 250 ml. of anhydrous 1,2‐dimethoxyethane

solvent: 108 g. (100 ml., 1.00 mole) of cold (0°), freshly distilled acetic anhydride

intermediate: 2‐acetoxy‐
trans
‐1‐phenylpropene

catalyst: 0.202 mole of anhydrous zinc chloride

reactant: 14.50 g. (0.2014 mole) of freshly distilled butyraldehyde

product:
threo
‐4‐hydroxy‐3‐phenyl‐2‐heptanone
1‐Benzylindole
Authors: Heaney Harry , Ley Steven V.
Published: November 2003

1‐Benzylindole

product: 1‐benzylindole
Fragmentation of α,β‐Epoxyketones to Acetylenic Aldehydes and Ketones: Preparation of 2,3‐Epoxycyclohexanone and its Fragmentation to 5‐Hexynal
Authors: Felix Dorothee , Wintner Claude , Eschenmoser A.
Published: November 2003

Fragmentation of α,β‐epoxyketones to acetylenic aldehydes and ketones: preparation of 2,3‐epoxycyclohexanone and its fragmentation to 5‐hexynal

product: 2,3‐epoxycyclohexanone

reactant: 20 ml. of diethyl phthalate

product: 5‐hexynal
2‐Iodo‐
p
‐Xylene
Authors: Taylor Edward C. , Kienzle Frank , McKillop Alexander
Published: November 2003

2‐Iodo‐
p
‐xylene

reactant: 2‐iodo‐
p
‐xylene
Methyl 2‐Alkynoates from 3‐Alkyl‐2‐Pyrazolin‐5‐ones: Methyl 2‐Hexynoate
Authors: Taylor Edward C. , Robey Roger L. , Johnson David K. , McKillop Alexander
Published: November 2003

Methyl 2‐Alkynoates from 3‐Alkyl‐2‐Pyrazolin‐5‐ones: Methyl 2‐Hexynoate

intermediate: 3‐(1‐propyl)‐2‐pyrazolin‐5‐one

product: methyl 2‐hexynoate
Methyl Nitroacetate
Authors: Zen S. , Koyama M. , Koto S.
Published: November 2003

Methyl Nitroacetate

intermediate: dipotassium salt of nitroacetic acid

product: methyl nitroacetate
(
S
)‐(−)‐α‐(1‐Naphthyl)Ethylamine
Authors: Mohacsi E. , Leimgruber W.
Published: November 2003

(
S
)‐(−)‐α‐(1‐naphthyl)ethylamine

product: (
S
)‐(−)‐α‐(1‐
Naphthyl)ethylamine

reactant: 58.44 g. (0.1849 mole) of (−)‐2,3:4,6‐di‐
O
‐isopropylidene‐2‐keto‐
L
‐gulonic acid hydrate [(−)‐DAG]

reactant: 34.24 g. (0.2002 mole) of racemic α‐(1‐naphthyl)ethylamine

intermediate: (−)‐amine (−)‐DAG
2‐Phenyl‐2‐Vinylbutyronitrile
Authors: Makosza M. , Czyzewski J. , Jawdosiuk M.
Published: November 2003

2‐Phenyl‐2‐vinylbutyronitrile

product: 2‐phenyl‐2‐vinylbutyronitrile
Sulfide Contraction
via
Alkylative Coupling: 3‐Methyl‐2,4‐Heptanedione
Authors: Loeliger P. , Flückiger E.
Published: November 2003

Sulfide contraction
via
alkylative coupling: 3‐methyl‐2,4‐heptanedione

intermediate: 3‐chloro‐
N,N
‐dimethyl‐1‐propylamine

intermediate: bis(3‐dimethylaminopropyl)phenylphosphine

intermediate: S‐(2‐
Oxobut
‐3‐
yl
)
Butanethioate

reactant: 10.4 g. (0.100 mole) of thiobutyric acid

product: 3‐methyl‐2,4‐heptanedione
ortho‐Alkylation of Anilines: Ethyl 4‐Amino‐3‐Methylbenzoate
Authors: Gassman P. G. , Gruetzmacher G.
Published: November 2003

ortho‐Alkylation of anilines: ethyl 4‐amino‐3‐methylbenzoate

reactant: 16.50 g. (0.1000 mole) of ethyl 4‐aminobenzoate (Benzocaine, )

intermediate: ethyl 4‐amino‐3‐(methylthiomethyl)benzoate

product: ethyl 4‐amino‐3‐methylbenzoate
Alkylation of Isoquinolinesvia2‐Benzoyl‐1,2‐dihydroisoquinaldonitriles: 1‐Benzylisoquinoline
Authors: Uff Barrie C. , Kershaw John R. , Neumeyer John L.
Published: November 2003

Alkylation of isoquinolinesvia2‐benzoyl‐1,2‐dihydroisoquinaldonitriles: 1‐Benzylisoquinoline

intermediate: 2‐benzoyl‐1,2‐dihydroisoquinaldonitrile

product: 1‐benzylisoquinoline

intermediate: 1‐benzyl‐2‐benzoyl‐1,2‐dihydroisoquinaldonitrile
Conversion of Primary Alcohols to Urethanes
via
the Inner Salt of Methyl (Carboxysulfamoyl)Triethylammonium Hydroxide: Methyl
n
‐Hexylcarbamate
Authors: Burgess Edward M. , Penton Harold R. , Taylor E. Alan , Williams W. Michael
Published: November 2003

Conversion of primary alcohols to urethanes
via
the inner salt of Methyl (Carboxysulfamoyl)Triethylammonium hydroxide: Methyl
n
‐Hexylcarbamate

intermediate: methyl (chlorosulfonyl)carbamate

byproduct: triethylamine hydrochloride

intermediate: methyl (carboxysulfamoyl)triethylammonium hydroxide

product: methyl
n
‐hexylcarbamate
Free‐Radical Alkylation of Quinones: 2‐Phenoxymethyl‐1,4‐Benzoquinone
Authors: Jacobsen Niels
Published: November 2003

Free‐radical alkylation of quinones: 2‐phenoxymethyl‐1,4‐benzoquinone

product: 2‐phenoxymethyl‐1,4‐benzoquinone

reactant: Fluka purum grade benzoquinone

solvent: petroleum ether (b.p. 60°)

product: 2‐tert‐Butyl

product: 2‐Benzyl

product: 2‐(α‐Chloroethyl)

product: 2‐Methoxymethyl

product: 2‐(ω‐Carboxybutyl)

product: 2‐Cyclopropyl‐3‐methyl

product: 2‐Acetoxy‐3‐(γ,γ‐dimethylallyl)
Reductive Cleavage of Allylic Alcohols, Ethers, or Acetates to Olefins: 3‐Methylcyclohexene
Authors: Elphimoff‐Felkin I. , Sarda P.
Published: November 2003

Reductive cleavage of allylic alcohols, ethers, or acetates to olefins: 3‐methylcyclohexene

intermediate: 3‐methyl‐2‐cyclohexen‐1‐ol

reactant: zinc amalgam

product: 3‐methylcyclohexene
2,3,4,5‐Tetrahydropyridine Trimer
Authors: Claxton George P. , Allen Lloyd , Grisar J. Martin
Published: November 2003

2,3,4,5‐Tetrahydropyridine trimer

product: 2,3,4,5‐
Tetrahydropyridine trimer

intermediate: Isotripiperidein

product: β‐ (m.p. 70–73°) tripiperidein

product: α‐Tripiperidein
Acyloin Condensation in which Chlorotrimethylsilane is used as a Trapping Agent: 1,2‐Bis(trimethylsilyloxy)cyclobutene and 2‐Hydroxycyclobutanone
Authors: Bloomfield Jordan J. , Nelke Janice M.
Published: November 2003

Acyloin condensation in which chlorotrimethylsilane is used as a trapping agent: 1,2‐bis(trimethylsilyloxy)cyclobutene and 2‐hydroxycyclobutanone

product: 1,2‐
Bis(trimethylsilyloxy)cyclobutene

product: 2‐hydroxycyclobutanone
Alkylation of Dimedone with a Tricarbonyl(diene)iron Complex: Tricarbonyl[2‐[(2,3,4,5‐η)‐4‐Methoxy‐2,4‐Cyclohexadien‐1‐yl]‐5,5‐Dimethyl‐1,3‐Cyclohexanedione]Iron
Authors: Birch A. J. , Chamberlain K. B.
Published: November 2003

Alkylation of dimedone with a tricarbonyl(diene)iron complex: tricarbonyl[2‐[(2,3,4,5‐η)‐4‐methoxy‐2,4‐cyclohexadien‐1‐yl]‐5,5‐dimethyl‐1,3‐cyclohexanedione]iron

product: Tricarbonyl[2‐[(2,3,4,5‐η)‐4‐Methoxy‐2,4‐Cyclohexadien‐1‐yl]‐5,5‐Dimethyl‐1,3‐Cyclohexanedione]Iron
Biaryls from Simple Arenes
via
Organotellurium Intermediates: 4,4′‐Dimethoxy‐1,1′‐Biphenyl
Authors: Bergman J. , Carlsson R. , Sjöberg B.
Published: November 2003

Biaryls from simple arenes
via
organotellurium intermediates: 4,4′‐dimethoxy‐1,1′‐biphenyl

product: 4,4′‐
Dimethoxy
‐1,1′‐
biphenyl

intermediate: 20.6 g. (0.0497 mole) of bis(4‐methoxyphenyl)tellurium dichloride

product: diphenyltellurium dichloride
18‐Crown‐6
Authors: Gokel George W. , Cram Donald J. , Liotta Charles L. , Harris Henry P. , Cook Fred L.
Published: November 2003

18‐crown‐6

product: 18‐crown‐6
1‐Ethoxy‐1‐Butyne
Authors: Newman Melvin S. , Stalick W. M.
Published: November 2003

1‐Ethoxy‐1‐butyne

product: 1‐ethoxy‐1‐butyne
Monoalkylation of α,β‐Unsaturated Ketones
via
Metalloenamines: 1‐Butyl‐10‐methyl‐Δ
1(9)
‐2‐octalone
Authors: Stork G. , Benaim J.
Published: November 2003

Monoalkylation of α,β‐unsaturated ketones
via
metalloenamines: 1‐butyl‐10‐methyl‐Δ
1(9)
‐2‐octalone

reactant: 7.4 g. (0.045 mole) of 10‐methyl‐Δ
1(9)
‐2‐octalone

intermediate: 6.12 g. (0.0297 mole) of 10‐methyl‐Δ1(9)‐2‐octalone N,N‐dimethylhydrazone

product: 1‐butyl‐10‐methyl‐Δ1(9)‐2‐octalone
p
‐Tolylsulfonyldiazomethane
Authors: van Leusen A. M. , Strating J.
Published: November 2003

p
‐Tolylsulfonyldiazomethane

intermediate:
Ethyl
N‐(p‐
tolylsulfonylmethyl
)
carbamate

intermediate:
Ethyl
N‐
nitroso
‐N‐(p‐
tolylsulfonylmethyl
)
carbamate

product: p‐
Tolylsulfonyldiazomethane

reactant: Ethyl carbamate (J. T. Baker Chemical Company)

product: chloro‐
p
‐tolylsulfonyl‐
p
‐tolylthiomethane

product:
N
‐hydroxy‐1‐(
p
‐tolysulfonyl)methanimidoyl chloride

product: 1‐(1‐
tert
‐butoxy‐1‐chloromethysulfonyl)‐4‐methylbenzene

product: 1‐(1‐chloro‐1‐ethoxymethylsulfonyl)‐4‐methylbenzene

product: 1‐(4‐methoxyphenylsulfonyl)‐2,2,3,3‐tetramethylcyclopropane

product: (
d,l
)‐1‐(4‐methoxyphenylsulfonyl)‐
trans
‐2,3‐dimethylcyclopropane
3,5,5‐Trimethyl‐2‐(2‐Oxopropyl)‐2‐Cyclohexen‐1‐One
Authors: Valenta Z. , Liu H. J.
Published: November 2003

3,5,5‐Trimethyl‐2‐(2‐oxopropyl)‐2‐cyclohexen‐1‐one

intermediate: 7‐
Acetoxy
‐4,4,6,7‐
tetramethylbicyclo
[4.2.0]
octan
‐2‐
one

intermediate: 7‐
Hydroxy
‐4,4,6,7‐
tetramethylbicyclo
[4.2.0]
octan
‐2‐
one

product: 3,5,5‐
Trimethyl
‐2‐(2‐
oxopropyl
)‐2‐
cyclohexen
‐1‐
one

reactant: Isophorone obtained from M C and B Manufacturing Chemists
Allylically Transposed Amines from Allylic Alcohols: 3,7‐Dimethyl‐1,6‐Octadien‐3‐Amine
Authors: Clizbe Lane A. , Overman Larry E.
Published: November 2003

Allylically transposed amines from allylic alcohols: 3,7‐dimethyl‐1,6‐octadien‐3‐amine

intermediate:
Geraniol trichloroacetimidate
(1)

intermediate: 3,7‐
Dimethyl
‐3‐
trichloroacetamido
‐1,6‐
octadiene
(2)

solvent: 300 ml. of xylene

product: 3,7‐
Dimethyl
‐1,6‐
octadien
‐3‐
amine
(3)

product: 3‐Trichloroacetamido‐1‐hexene

product: 3‐Phenyl‐3‐trichloroacetamido‐1‐propene

product: (
E
)‐1‐Trichloroacetamido‐2‐heptene

product: 3‐Trichloroacetamido‐1‐cyclohexene

product: 3,7‐Dimethyl‐1‐trichloroacetamido‐2,6‐octadiene

product: 3,5,5‐Trimethyl‐3‐trichloroacetamido‐1‐cyclohexene

product: 3‐(4,4‐Ethylenedioxybutyl)‐3‐trichloroacetamido‐1‐cyclohexene
cis
‐Dichloroalkanes from Epoxides:
cis
‐1,2‐Dichlorocyclohexane
Authors: Oliver James E. , Sonnet Philip E.
Published: November 2003

cis
‐Dichloroalkanes from epoxides:
cis
‐1,2‐dichlorocyclohexane

product:
cis
‐1,2‐dichlorocyclohexane
Radical Anion Arylation: Diethyl Phenylphosphonate
Authors: Bunnett Joseph F. , Weiss Robert H.
Published: November 2003

Radical anion arylation: diethyl phenylphosphonate

product: diethyl phenylphosphonate
Sulfide Synthesis in Preparation of Dialkyl and Alkyl Aryl Sulfides: Neopentyl Phenyl Sulfide
Authors: Landini D. , Rolla F.
Published: November 2003

Sulfide synthesis in preparation of dialkyl and alkyl aryl sulfides: neopentyl phenyl sulfide

catalyst: 1.67 g. (0.00329 mole) of tributylhexadecylphosphonium bromide

product: neopentyl phenyl sulfide
2‐Trimethylsilyloxy‐1,3‐Butadiene as a Reactive Diene: Diethyl
trans
‐4‐Trimethylsilyloxy‐4‐Cyclohexene‐1,2‐Dicarboxylate
Authors: Jung Michael E. , McCombs Charles A.
Published: November 2003

2‐Trimethylsilyloxy‐1,3‐butadiene as a reactive diene: diethyl
trans
‐4‐trimethylsilyloxy‐4‐cyclohexene‐1,2‐dicarboxylate

intermediate: 2‐
Trimethylsilyloxy
‐1,3‐
butadiene
(1)

product:
Diethyl
trans‐4‐
trimethylsilyloxy
‐4‐
cyclohexene
‐1,2‐
dicarboxylate
(2)
Cleavage of Methyl Ethers with Iodotrimethylsilane: Cyclohexanol from Cyclohexyl Methyl Ether
Authors: Jung Michael E. , Lyster Mark A.
Published: November 2003

Cleavage of methyl ethers with iodotrimethylsilane: cyclohexanol from cyclohexyl methyl ether

reactant: 16.2 g. (0.100 mole) of hexamethyldisiloxane

intermediate: iodotrimethylsilane

reactant: 1.722 g. (0.01524 mole) of cyclohexyl methyl ether

product: cyclohexanol
Cyanide‐Catalyzed Conjugate Addition of Aryl Aldehydes: 4‐oxo‐4‐(3‐Pyridyl)Butyronitrile
Authors: Stetter H. , Kuhlmann H. , Lorenz G.
Published: November 2003

Cyanide‐Catalyzed Conjugate Addition of Aryl Aldehydes: 4‐OXO‐4‐(3‐PYRIDYL)BUTYRONITRILE

reactant: 107.1 g. (1.001 mole) of 3‐pyridinecarboxaldehyde

product: 4‐oxo‐4‐(3‐pyridyl)butyronitrile

product: R1 = C6H5, R2 = R3 = H

product: R1 = C6H5, R2 = H, R3 = CH3

product: R1 = C6H5, R2 = CH3, R3 = H

product: R1 = R2 = C6H5, R3 = H

product: R1 = 4‐ClC6H4, R2 = R3 = H
One‐Carbon Ring Expansion of Cycloalkanones to Conjugated Cycloalkenones: 2‐Cyclohepten‐1‐One
Authors: Ito Yoshihiko , Fujii Shotaro , Nakatuska Masashi , Kawamoto Fumio , Saegusa Takeo
Published: November 2003

One‐carbon ring expansion of cycloalkanones to conjugated cycloalkenones: 2‐cyclohepten‐1‐one

intermediate: 1‐trimethylsilyloxycyclohexene

reactant: 18.5 g. (0.146 mole) of diethylzinc

reactant: 40.2 g. (0.150 mole) of diiodomethane

intermediate: 1‐trimethylsilyloxybicyclo[4.1.0]heptane

product: 2‐cyclohepten‐1‐one

byproduct: 3‐chlorocycloheptanone
Rearrangement of Bridgehead Alcohols to Polycyclic Ketones by Fragmentation‐Cyclization: 4‐Protoadamantanone (Tricyclo‐[4.3.1.0
3,8
]Decan‐4‐One)
Authors: Majerski Zdenko , Hameršak Zdenko
Published: November 2003

Rearrangement of bridgehead alcohols to polycyclic ketones by fragmentation‐cyclization: 4‐protoadamantanone (tricyclo‐[4.3.1.0
3,8
]decan‐4‐one)

intermediate: endo‐7‐
Iodomethylbicyclo
[3.3.1]
nonan
‐3‐
one

product: 4‐protoadamantanone
Thiazoles from Ethyl Isocyanoacetate and Thiono Esters: Ethyl Thiazole‐4‐Carboxylate
Authors: Hartman G. D. , Weinstock L. M.
Published: November 2003

Thiazoles from ethyl isocyanoacetate and thiono esters: ethyl thiazole‐4‐carboxylate

intermediate:N‐formylglycine ethyl ester

intermediate: ethyl isocyanoacetate

intermediate:O‐ethyl thioformate

product: ethyl thiazole‐4‐carboxylate

byproduct: ethyl formate
Trichloromethyl Chloroformate as a Phosgene Equivalent: 3‐Isocyanatopropanoyl Chloride
Authors: Kurita Keisuke , Iwakura Yoshio
Published: November 2003

Trichloromethyl chloroformate as a phosgene equivalent: 3‐isocyanatopropanoyl chloride

intermediate:
Trichloromethyl chloroformate

product: 3‐
Isocyanatopropanoyl chloride

reactant: 3‐aminopropanoic acid hydrochloride
Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid
Authors: Lee Donald G. , Lamb Shannon E. , Chang Victor S.
Published: November 2003

Carboxylic acids from the oxidation of terminal alkenes by permanganate: nonadecanoic acid

product: nonadecanoic acid

product: Heneicosanoic acid

product: Nonadecanoic acid

product: Heptadecanoic acid

product: Pentadecanoic acid

product: Tridecanoic acid

product: Nonanoic acid

product: Heptanoic acid

product: Benzoic acid
1,2‐Cyclobutanedione
Authors: Denis J. M. , Champion J. , Conia J. M.
Published: November 2003

1,2‐Cyclobutanedione

product: 1,2‐cyclobutanedione
Imidazole‐2‐Carboxaldehyde
Authors: Bastiaansen Leonard A. M. , Lier Pieter M. Van , Godefroi Erik F.
Published: November 2003

Imidazole‐2‐carboxaldehyde

intermediate: 150 g (0.335 mol) of dry, unrecrystallized 1‐benzoyl‐2‐(1,3‐dibenzoyl‐4‐imidazolin‐2‐yl) imidazole

intermediate: 38.0 g (0.10 mol) of dry, unrecrystallized 2‐(1,3‐dibenzoyl‐4‐imidazolin‐2‐yl)imidazole hydrochloride

intermediate: 19.1 g (0.05 mol) of dry, unrecrystallized 2‐(1,3‐dibenzoylimidazolidin‐2‐yl) imidazole hydrochloride in 200 mL of concentrated hydrochloric acid

product: imidazole‐2‐carboxaldehyde
(R,S)‐Mevalonolactone‐2‐13C
Authors: Tanabe Masato , Peters Richard H.
Published: November 2003

(R,S)‐Mevalonolactone‐2‐13C

reactant: 4.40 g (0.050 mol) of 4‐hydroxy‐2‐butanone

catalyst: 13.9 g (0.060 mol) of freshly prepared silver oxide

reactant: 12.0 g (0.070 mol) of benzyl bromide

intermediate: 4‐benzyloxy‐2‐butanone

reactant: 0.439 g (0.00720 mol) of acetic acid‐2‐13C

intermediate: 0.519 g (0.00217 mol) of 5‐benzyloxy‐3‐hydroxy‐3‐methylpentanoic acid‐2‐13C

product: mevalonolactone‐2‐13C
Acid Chlorides from α‐Keto Acids with α,α‐Dichloromethyl Methyl Ether: Pyruvoyl Chloride
Authors: Ottenheijm Harry C. J. , Tijhuis Marianne W.
Published: November 2003

Acid chlorides from α‐keto acids with α,α‐dichloromethyl methyl ether: Pyruvoyl chloride

reactant: 35.2 g (28.6 mL, 0.40 mol) of pyruvic acid

reactant: 46.4 g (36.1 mL, 0.40 mol) of α,α‐dichloromethyl methyl ether

byproduct: methyl formate

product: pyruvoyl chloride

product: 2‐oxobutanoyl chloride

product: 3‐methyl‐2‐oxobutanoyl chloride

product: phenylglyoxylyl chloride
Aliphatic and Aromatic β‐Keto Esters from Monoethyl Malonate: Ethyl 2‐butyrylacetate
Authors: Wierenga W. , Skulnick H. I.
Published: November 2003

Aliphatic and aromatic β‐keto esters from monoethyl malonate: ethyl 2‐butyrylacetate

product: ethyl 2‐butyrylacetate
Preparation of
O
‐Esters from the Corresponding Thiol Esters:
tert
‐Butyl Cyclohexanecarboxylate
Authors: Chan Wan Kit , Masamune S. , Spessard Gary O.
Published: November 2003

Preparation of
O
‐Esters from the corresponding thiol esters:
tert
‐butyl cyclohexanecarboxylate

product: tert‐butyl cyclohexanecarboxylate

unknown: C‐C6H11

unknown: (CH3)3C

unknown: (E)CH3CHCH

unknown: (Z)CH3CO2C(CH3)CH
Mercaptans from Thioketals: Cyclododecyl Mercaptan
Authors: Wilson S. R. , Georgiadis G. M.
Published: November 2003

Mercaptans from thioketals: cyclododecyl mercaptan

reactant: 46.5 g (0.26 mol) of cyclododecanone

intermediate: 25.8 g (0.10 mol) of 1,4‐dithiaspiro[4.11]hexadecane

product: cyclododecyl mercaptan

reactant: 4‐tert‐Butylcyclohexanone

reactant: 2‐Adamantanone

reactant: 4‐Heptanone

reactant: Acetophenone

reactant: Cyclohexanone

reactant: Estrone

reactant: Pregnenolone

reactant: Undecan‐5‐one
1,3‐Oxazepines via Photoisomerization of Heteroaromatic
N
‐Oxides: 3,1‐Benzoxazepine
Authors: Albini Angelo , Bettinetti Gian Franco , Minoli Giovanna
Published: November 2003

1,3‐Oxazepines via photoisomerization of heteroaromatic
N
‐oxides: 3,1‐benzoxazepine

product: 3,1‐benzoxazepine

byproduct: carbostyril, that is, 2(1H)‐quinolinone
Reductive Cleavage of Vinyl Phosphorodiamidates: 17β‐
tert
‐Butoxy‐Gα‐androst‐2‐ene
Authors: Ireland Robert E. , O'Neil Thomas H. , Tolman Glen L.
Published: November 2003

Reductive cleavage of vinyl phosphorodiamidates: 17β‐
tert
‐butoxy‐Gα‐androst‐2‐ene

intermediate: vinyl phosphorodiamidate

intermediate: 1.61 g (4.6 mmol) of 17β‐tert‐butoxy‐5α‐androstan‐3‐one

reactant: N,N,N′,N′‐Tetramethyldiamidophosphorochloridate, 5.83 mL (0.038 mol)

product: 17β‐tert‐butoxy‐5α‐androst‐2‐ene
Palladium‐Catalyzed Synthesis of 1,4‐Dienes by Allylation of Alkenylalanes:α‐Farnesene
Authors: Negishi Ei‐ichi , Matsushita Hajime
Published: November 2003

Palladium‐catalyzed synthesis of 1,4‐dienes by allylation of alkenylalanes:α‐farnesene

product: α‐farnesene

product: 6‐Z isomer of α‐farnesene
Reductive Arylation of Electron‐Deficient Olefins: 4‐(4‐Chlorophenyl)butan‐2‐one
Authors: Citterio Attilio
Published: November 2003

Reductive arylation of electron‐deficient olefins: 4‐(4‐chlorophenyl)butan‐2‐one

product: 4‐(4‐chlorophenyl)butan‐2‐one

product: semicarbazone
Preparation of Low‐Halide Methyllithium
Authors: Lusch Michael J. , Phillips William V. , Sieloff Ronald F. , Nomura Glenn S. , House Herbert O.
Published: November 2003

Preparation of Low‐Halide Methyllithium

reactant: methyl chloride

product: methyllithium

unknown: 1.0 mL of freshly distilled 1,2‐dibromoethane
Synthesis and
D
iels–
A
lder Reactions of 3‐Acetyl‐2(3
H
)‐oxazolone: 6‐Amino‐3,4‐dimethyl‐
cis
‐3‐cyclohexen‐1‐ol
Authors: Scholz Karl‐Heinz , Heine Hans‐Georg , Hartmann Willy
Published: November 2003

Synthesis and Diels–Alder reactions of 3‐acetyl‐2(3
H
)‐oxazolone: 6‐amino‐3,4‐dimethyl‐
cis
‐3‐cyclohexen‐1‐ol

intermediate: 326 g (3.75 mol) of 2‐oxazolidinone

intermediate: 258 g (2.0 mol) of 3‐acetyl‐2‐oxazolidinone

intermediate: 4‐Acetyl‐7,8‐dimethyl‐2‐oxa‐4‐azabicyclo[4.3.0]non‐7‐en‐3‐one.

product: 63.5 g (0.5 mol) of 3‐acetyl‐2(3H)‐oxazolone

product: 6‐Amino‐3,4‐dimethyl‐cis‐3‐cyclohexen‐1‐ol.
Thiation with 2,4‐Bis(4‐Methoxyphenyl)‐1,3,2,4‐ Dithiadiphosphetane 2,4‐Disulfide:N‐Methylthiopyrrolidone
Authors: Thomsen I. , Clausen K. , Scheibye S. , Lawesson S.‐O.
Published: November 2003

Thiation with 2,4‐bis(4‐methoxyphenyl)‐1,3,2,4‐ dithiadiphosphetane 2,4‐disulfide:N‐methylthiopyrrolidone

reactant: 111.0 g (0.25 mol) of phosphorus sulfide, P4S10

intermediate: 2,4‐bis(4‐methoxyphenyl)‐1,3,2,4‐dithiadiphosphetane 2,4‐disulfide

product: N‐methylthiopyrrolidone
Acyloin Condensation by Thiazolium Ion Catalysis: Butyroin
Authors: Stetter H. , Kuhlmann H.
Published: November 2003

Acyloin condensation by thiazolium ion catalysis: butyroin

catalyst: 13.4 g (0.05 mol) of 3‐benzyl‐5‐(2‐hydroxyethyl)‐4‐methyl‐1,3‐thiazolium chloride

product: butyroin

product: furoin
Synthesis of α,β‐Unsaturated Nitriles from Acetonitrile: Cyclohexylideneacetonitrile and Cinnamonitrile
Authors: DiBiase Stephen A. , Beadle James R. , Gokel George W.
Published: November 2003

Synthesis of α,β‐unsaturated nitriles from acetonitrile: cyclohexylideneacetonitrile and cinnamonitrile

product: cinnamonitrile

intermediate: cyclohexylideneacetonitrile
in situ
Cyanosilylation of Carbonyl Compounds:
O
‐Trimethylsilyl‐4‐Methoxymandelonitrile
Authors: Rasmussen J. K. , Heilmann S. M.
Published: November 2003

in situ cyanosilylation of carbonyl compounds:
O
‐trimethylsilyl‐4‐methoxymandelonitrile

product: colorless liquid

unknown: R
1
 = C
6
H
5
, R
2
 = H

unknown: R
1
 = 4‐CH
3
C
6
H
4
, R
2
 = H

unknown: R
1
 = 2‐ClC
6
H
4
, R
2
 = H

unknown: R
1
 = 4‐ClC
6
H
4
, R
2
 = H

unknown: R
1
 = C
6
H
5
, R
2
 = CH
3

unknown: R
1
, R
2
 = (CH
2
)5

unknown: R
1
 = 
c
‐C
6
H
11
, R
2
 = H
Asymmetric Hydrogenation of Ketopantoyl Lactone:D‐(−)‐Pantoyl Lactone
Authors: Ojima I. , Kogure T. , Yoda Y.
Published: November 2003

Asymmetric hydrogenation of ketopantoyl lactone:D‐(−)‐pantoyl lactone

reactant: 25.6 g (0.2 mol) of ketopantoyl lactone

product:D‐(−)‐pantoyl lactone
Optically Active Epoxides from Vicinal Diols via Vicinal Acetoxy Bromides: (
S
)‐( − )‐ and (
R
)‐( + )‐Methyloxirane
Authors: Ellis Martin K. , Golding Bernard T.
Published: November 2003

Optically active epoxides from vicinal diols via vicinal acetoxy bromides: (
S
)‐( − )‐ and (
R
)‐( + )‐methyloxirane

intermediate: (S)‐( + )‐propane‐1,2‐diol

intermediate: (S)‐( − )‐2‐acetoxy‐1‐bromopropane

product: (S)‐( − )‐methyloxirane

intermediate: (R)‐( + )‐2‐Acetoxy‐1‐bromopropane

product: (R)‐( + )‐Methyloxirane
Cyclopropanone Ethyl Hemiacetal from Ethyl 3‐Chloropropanoate
Authors: Salaün J. , Marguerite J.
Published: November 2003

Cyclopropanone ethyl hemiacetal from ethyl 3‐chloropropanoate

intermediate: 1‐ethoxy‐1‐(trimethylsilyloxy) cyclopropane

product: Cyclopropanone ethyl hemiacetal
Hexafluoroacetone
Authors: Puy Michael Van Der , Anello Louis G.
Published: November 2003

Hexafluoroacetone

intermediate: 60 g (0.165 mol) of 2,2,4,4‐tetrakis(trifluoromethyl)‐1,3‐dithietane

product: hexafluoroacetone (HFA)
Peptide Synthesis using 1‐(4‐Chlorophenyl)‐3‐(4′‐Methyl‐1′‐Piperazinyl)‐2‐Propyn‐1‐one as Reagent: Benzyloxycarbonyl‐
L
‐Alanyl‐
L
‐Cysteine Methyl Ester and Benzyloxycarbonyl‐
L
‐Aspartyl‐(
tert
‐Butyl Ester)‐
L
‐Phenylalanyl‐
L
‐Valine Methyl Ester
Authors: Fahrni H. P. , Lienhard U. , Neuenschwander M.
Published: November 2003

Peptide synthesis using 1‐(4‐chlorophenyl)‐3‐(4′‐methyl‐1′‐piperazinyl)‐2‐propyn‐1‐one as reagent: benzyloxycarbonyl‐
L
‐alanyl‐
L
‐cysteine methyl ester and benzyloxycarbonyl‐
L
‐aspartyl‐(
tert
‐butyl ester)‐
L
‐phenylalanyl‐
L
‐valine methyl ester

product: benzyloxycarbonyl‐L‐alanyl‐L‐cysteine methyl ester

product: benzyloxycarbonyl‐L‐aspartyl‐(tert‐butyl ester)‐L‐phenylalanyl‐L‐valine methyl ester

product: Cbz‐L‐Ala‐Gly‐OMe

product: Cbz‐L‐Ala‐L‐Val‐OMe

product: Cbz‐L‐Ala‐L‐Phe‐OMe

product: Cbz‐Gly‐L‐Phe‐Gly‐OEt

product: Cbz‐L‐Asp(O‐t‐Bu)‐L‐Phe‐L‐Val‐OMe

product: Cbz‐L‐Ile‐L‐Ile‐OBzl

product: Cbz‐L‐Ala‐L‐Ser‐OMe

product: Cbz‐L‐Ala‐L‐Tyr‐OMe

product: Cbz‐L‐Ala‐L‐Cys‐OMe

product: Cbz‐L‐Ala‐L‐Met‐OMe

product: Cbz‐L‐Ser‐Gly‐OEt
Hexahydro‐2‐(1
H
)‐Azocinone
Authors: Olah George A. , Fung Alexander P.
Published: November 2003

Hexahydro‐2‐(1
H
)‐azocinone

reactant: cycloheptanone (5.61 g, 0.05 mol)

product: hexahydro‐2(1H)‐azocinone
Indoles from 2‐Methylnitrobenzenes by Condensation with Formamide Acetals Followed by Reduction: 4‐Benzyloxyindole
Authors: Batcho Andrew D. , Leimgruber Willy
Published: November 2003

Indoles from 2‐Methylnitrobenzenes by Condensation with Formamide Acetals Followed by Reduction: 4‐Benzyloxyindole

intermediate: 6‐benzyloxy‐2‐nitrotoluene

intermediate: (E)‐6‐benzyloxy‐2‐nitro‐β‐pyrrolidinostyrene and (E)‐6‐benzyloxy‐β‐dimethylamino‐2‐nitrostyrene

product: 4‐benzyloxyindole

intermediate: pyrrolidine enamine, mp 108–110° (MeOH), and N,N‐dimethylenamine
Addition of an Ethylcopper Complex to 1‐Octyne: (
E
)‐5‐Ethyl‐1,4‐Undecadiene
Authors: Iyer Ramnath S. , Helquist Paul
Published: November 2003

Addition of an ethylcopper complex to 1‐octyne: (
E
)‐5‐ethyl‐1,4‐undecadiene

product: (
E
)‐5‐ethyl‐1,4‐undecadiene
α‐Amino Acetals: 2,2‐Diethoxy‐2‐(4‐Pyridyl)Ethylamine
Authors: LaMattina John L. , Suleske R. T.
Published: November 2003

α‐Amino acetals: 2,2‐diethoxy‐2‐(4‐pyridyl)ethylamine

reactant: Hydroxylamine hydrochloride (25.0 g, 0.36 mol)

reactant: 4‐acetylpyridine (36.3 g, 0.30 mol)

intermediate:
E
‐ and
Z
‐isomers of 4‐acetylpyridine oxime

intermediate:
E
‐4‐acetylpyridine oxime

product: 2,2‐Diethoxy‐2‐(4‐pyridyl)ethylamine.

intermediate:
E
)‐4‐acetylpyridine tosylate (55.1 g, 0.19 mol
Condensation of Dimethyl 1,3‐Acetonedicarboxylate with 1,2‐Dicarbonyl Compounds:
cis
‐bicyclo[3.3.0]octane‐3,7‐diones
Authors: Bertz Steven H. , Cook James M. , Gawish Ali , Weiss Ulrich
Published: November 2003

Condensation of Dimethyl 1,3‐Acetonedicarboxylate with 1,2‐Dicarbonyl Compounds:
cis
‐Bicyclo[3.3.0]octane‐3,7‐diones

intermediate: Tetramethyl 3,7‐dihydroxybicyclo[3.3.0]octa‐2,6‐diene‐2,4,6,8‐tetracarboxylate

product: cis‐Bicyclo[3.3.0]octane‐3,7‐dione

intermediate: Tetramethyl 3,7‐dihydroxy‐1,5‐dimethylbicyclo[3.3.0]octa‐2,6‐diene‐2,4,6,8‐tetracarboxylate

product: cis‐1,5‐Dimethylbicyclo[3.3.0]octane‐3,7‐dione

intermediate: C16H16O10Na2·H2O
Conversion of Epoxides to β‐Hydroxy Isocyanides:
trans
‐2‐Isocyanocyclohexanol
Authors: Gassman Paul G. , Guggenheim Thomas L.
Published: November 2003

Conversion of epoxides to β‐hydroxy isocyanides:
trans
‐2‐isocyanocyclohexanol

intermediate: [(trans‐2‐isocyanocyclohexyl)oxy]trimethylsilane

product: trans‐2‐isocyanocyclohexanol
Di‐
tert
‐Butyl Methylenemalonate
Authors: Ballesteros Paloma , Roberts Bryan W.
Published: November 2003

Di‐
tert
‐butyl methylenemalonate

product: Di‐
tert
‐butyl methylenemalonate
The
S
tork–
D
anheiser Kinetic Alkylation Procedure: 3‐Ethoxy‐6‐methyl‐2‐cyclohexen‐1‐one
Authors: Kende Andrew S. , Fludzinski Pawel
Published: November 2003

The Stork–Danheiser kinetic alkylation procedure: 3‐Ethoxy‐6‐methyl‐2‐cyclohexen‐1‐one

product: 3‐ethoxy‐6‐methyl‐2‐cyclohexen‐1‐one
Ethyl 4‐hydroxycrotonate
Authors: Kende Andrew S. , Fludzinski Pawel
Published: November 2003

Ethyl 4‐hydroxycrotonate

product: ethyl 4‐hydroxycrotonate
Hydroxylation of Enolates with Oxodiperoxymolybdenum(Pyridine)(Hexamethylphosphoric Triamide), MoO
5
·Py·HMPA(MoOPH): 3‐Hydroxy‐1,7,7‐Trimethylbicyclo[2.2.1]Heptan‐2‐one
Authors: Vedejs Edwin , Larsen S.
Published: November 2003

Hydroxylation of enolates with oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide), MoO
5
·Py·HMPA(MoOPH): 3‐hydroxy‐1,7,7‐trimethylbicyclo[2.2.1]heptan‐2‐one

intermediate: Oxodiperoxymolybdenum(aqua)(hexamethylphosphoric triamide), MoO5·H2O·HMPA

intermediate: Oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide) MoO5·Py·HMPAMoOPH

product: 1,7,7‐trimethyl‐3‐hydroxybicyclo[2.2.1]‐heptan‐2‐one
α‐Hydroxylation of a Ketone Using
o
‐Iodosylbenzoic Acid: α‐Hydroxyacetophenone via the α‐Hydroxy Dimethylacetal
Authors: Moriarty Robert M. , Hou Kwang‐Chung , Prakash Indra , Arora S. K.
Published: November 2003

α‐Hydroxylation of a ketone using
o
‐iodosylbenzoic acid: α‐hydroxyacetophenone via the α‐hydroxy dimethylacetal

reactant: Anhydrous methanol (80 mL)

product: α‐Hydroxyacetophenone.

intermediate: 6.0 g (0.33 mol) of α‐hydroxy dimethylacetal
Stereocontrolled Iodolactonization of Acyclic Olefinic Acids: The
trans
and
cis
Isomers of 4,5‐Dihydro‐5‐Iodomethyl‐4‐Phenyl‐2(3
H
)‐Furanone
Authors: Gonzalez F. Bermejo , Bartlett Paul A.
Published: November 2003

Stereocontrolled iodolactonization of acyclic olefinic acids: The
trans
and
cis
isomers of 4,5‐dihydro‐5‐iodomethyl‐4‐phenyl‐2(3
H
)‐furanone

intermediate: 3‐phenyl‐4‐pentenoic acid

product: trans iodolactone

product:
cis
‐iodolactone

product: methyl (3
RS
,4
RS
)‐4,5‐epoxy‐3‐phenylpentanoate
Stereospecific Reduction of Propargyl Alcohols: (
E
)‐3‐Trimethylsilyl‐2‐Propen‐1‐ol
Authors: Jones Todd K. , Denmark Scott E.
Published: November 2003

Stereospecific reduction of propargyl alcohols: (
E
)‐3‐trimethylsilyl‐2‐propen‐1‐ol

intermediate: 3‐trimethylsilyl‐2‐propyn‐1‐ol

product: (
E
)‐3‐trimethylsilyl‐2‐propen‐1‐ol
Tris(Dimethylamino)Sulfonium Difluorotrimethylsilicate
Authors: Middleton William J.
Published: November 2003

Tris(dimethylamino)sulfonium difluorotrimethylsilicate

product: tris(dimethylamino)sulfonium difluorotrimethylsilicate

reactant:N,N‐Dimethylaminotrimethylsilane is available from Petrarch Systems, Inc.

byproduct: hexamethyl‐disiloxane
The Stetter Reaction: 2,5‐Undecanedione and 3‐Methyl‐2‐Pentyl‐2‐Cyclopenten‐1‐one (Dihydrojasmone)
Authors: Stetter H. , Kuhlmann H. , Haese W.
Published: November 2003

The Stetter reaction: 2,5‐undecanedione and 3‐methyl‐2‐pentyl‐2‐cyclopenten‐1‐one (dihydrojasmone)

product: 3‐Methyl‐2‐pentyl‐2‐cyclopenten‐1‐one (Dihydrojasmone).

product: 2,5‐Undecanedione (92.1 g, 0.5 mol)
1,2,3,4,5‐Pentamethylcyclopentadiene
Authors: Threlkel Richard S. , Bercaw John E. , Seidler Paul F. , Stryker Jeffrey M. , Bergman Robert G.
Published: November 2003

1,2,3,4,5‐Pentamethylcyclopentadiene

product: 1,2,3,4,5‐Pentamethylcyclopentadiene
Alkoxycarbonylation of Propargyl Chloride: Methyl 4‐Chloro‐2‐butynoate
Authors: Olomucki M. , Gall J. Y. Le
Published: November 2003

Alkoxycarbonylation of propargyl chloride: methyl 4‐chloro‐2‐butynoate

product: methyl 4‐chloro‐2‐butynoate

product: 4‐Chloro‐2‐butynoic (chlorotetrolic) acid

product: ethyl 4‐chloro‐2‐butynoate

product: tert‐butyl 4‐chloro‐2‐butynoate
Trimethylsilylacetylene
Authors: Holmes Andrew B. , Sporikou Chris N.
Published: November 2003

Trimethylsilylacetylene

product: trimethylsilylacetylene
Dialkoxyacetylenes: di‐
tert
‐butoxyethyne, A Valuable Synthetic Intermediate
Authors: Bou Anna , Pericàs Miquel A. , Riera Antoni , Serratosa Fèlix
Published: November 2003

Dialkoxyacetylenes: di‐
tert
‐butoxyethyne, a valuable synthetic intermediate

intermediate:
trans
‐2,3‐dichloro‐1,4‐dioxane

intermediate:
trans
‐2‐
tert
‐butoxy‐3‐hydroxy‐1,4‐dioxane

intermediate:
trans
‐2,3‐di‐
tert
‐butoxy‐1,4‐dioxane

intermediate:
cis
‐ and
trans
‐2,3‐di‐
tert
‐butoxy‐1,4‐dioxane

intermediate: 1,2‐di‐
tert
‐butoxy‐1,2‐dichloroethane

intermediate: (
E
)‐1,2‐di‐
tert
‐butoxy‐1‐chloroethene

product: di‐
tert
‐butoxyethyne

byproduct: 0.1–0.5 g of
cis
‐2,3,7,10‐tetraoxabicyclo[4.4.0]decane

byproduct: (
Z
)‐1,2‐di‐
tert
‐butoxy‐1‐chloroethane

byproduct: 1,2,3‐tri‐
tert
‐butoxy‐3‐cyano‐1‐propene

byproduct: 1,2,3‐tri‐
tert
‐butoxy‐1‐cyano‐1‐propene
Ambient‐Temperature
U
llman Reaction: 4,5,4′,5′‐Tetramethoxy‐1,1′‐Biphenyl‐2,2′‐Dicarboxaldehyde
Authors: Ziegler F. E. , Fowler K. W. , Rodgers W. B. , Wester R. T.
Published: November 2003

Ambient‐temperature Ullman reaction: 4,5,4′,5′‐tetramethoxy‐1,1′‐biphenyl‐2,2′‐dicarboxaldehyde

intermediate: 6‐Bromo‐3,4‐dimethoxybenzaldehyde cyclohexylimine

reactant: cuprous iodidetriethyl phosphite complex

intermediate: 6‐iodoveratraldehyde cyclohexylimine

product: 4,5,4′,5′‐Tetramethoxy‐1,1′‐biphenyl‐2,2′‐carboxaldehyde (4)
Synthesis of a Key β‐Lactam Intermediate by a [2 + 2] Cycloaddition Route: 4‐Acetoxyazetidin‐2‐One
Authors: Mickel Stuart J. , Hsiao Shi‐Nung , Miller Marvin J.
Published: November 2003

Synthesis of a key β‐lactam intermediate by a [2 + 2] cycloaddition route: 4‐acetoxyazetidin‐2‐one

product: 4‐acetoxyazetidin‐2‐one
Synthesis of Macrocyclic Sulfides Using Cesium Thiolates: 1,4,8,11‐Tetrathiacyclotetradecane
Authors: Buter J. , Kellogg Richard M.
Published: November 2003

Synthesis of macrocyclic sulfides using cesium thiolates: 1,4,8,11‐tetrathiacyclotetradecane

intermediate: 3,7‐dithianonane‐1,9‐diol

intermediate: 3,7‐dithianonane‐1,9‐dithiol

product: 1,4,8,11‐tetrathiacyclotetradecane
(−)‐8‐phenylmenthol
Authors: Ort Oswald
Published: November 2003

(−)‐8‐phenylmenthol

intermediate: (2RS,5R)‐5‐Methyl‐2‐(1‐methyl‐1‐phenylethyl)cyclohexanone (2)

reactant: Grignard reagent

reactant: 40.0 g (0.26 mol) of (R)‐(+)‐pulegone

byproduct: biphenyl

product: (1RS,2SR,5R)‐5‐Methyl‐2‐(1‐methyl‐1‐phenylethyl)cyclohexanol (3/4)

intermediate: (1R,2S,5R)‐5‐Methyl‐2‐(1‐methyl‐1‐phenylethyl)cyclohexyl chloroacetate 5

product: (1R,2S,5R)‐5‐Methyl‐2‐(1‐methyl‐1‐phenylethyl)cyclohexanol (3)
Copper‐Catalyzed Conjugate Addition of a Zinc Homoenolate: Ethyl 3‐[3‐(trimethylsilyloxy)cyclohex‐2‐enyl]propionate
Authors: Nakamura Eiichi , Kuwajima Isao
Published: November 2003

Copper‐catalyzed conjugate addition of a zinc homoenolate: ethyl 3‐[3‐(trimethylsilyloxy)cyclohex‐2‐enyl]propionate

product: Ethyl 3‐[3‐(Trimethylsilyloxy)cyclohex‐2‐enyl]propionate

product: 1‐Trimethylsilyloxy‐1‐ethoxycyclopropane
Palladium‐Catalyzed Synthesis of Conjugated Dienes: (5Z,7E)‐5,7‐Hexadecadiene
Authors: Negishi Ei‐Ichi , Takahashi Tamotsu , Baba Shigeru
Published: November 2003

Palladium‐catalyzed synthesis of conjugated dienes: (5Z,7E)‐5,7‐hexadecadiene

intermediate: (E)‐1‐decenyldiisobutylalane

product: (5Z,7E)‐5,7‐hexadecadiene
Vinyl Radical Cyclization via Addition of Tin Radicals to Triple Bonds: 3‐Methylene‐4‐isopropyl‐1,1‐cyclopentanedicarboxylic Acid, Dimethyl Ester
Authors: Mook Robert , Sher Philip Michael
Published: November 2003

Vinyl radical cyclization via addition of tin radicals to triple bonds: 3‐Methylene‐4‐isopropyl‐1,1‐cyclopentanedicarboxylic acid, dimethyl ester

intermediate: (3‐Methyl‐2‐butenyl)propanedioic acid, dimethyl ester (1)

intermediate: (3‐Methyl‐2‐butenyl)(2‐propynyl)propanedioic acid, dimethyl ester (2)

intermediate: (
Z
)‐3‐Tributylstannylmethylene‐4‐isopropyl‐1,1‐cyclopentanedicarboxylic acid, dimethyl ester (3)

product: 3‐Methylene‐4‐isopropyl‐1,1‐cyclopentanedicarboxylic acid, dimethyl ester (4)
Vinylation of Enolates with a Vinyl Cation Equivalent:
trans
‐3‐Methyl‐2‐Vinylcyclohexanone
Authors: Chang Tony C. T. , Rosenblum Myron , Simms Nancy
Published: November 2003

Vinylation of enolates with a vinyl cation equivalent:
trans
‐3‐methyl‐2‐vinylcyclohexanone

intermediate: Dicarbonyl(cyclopentadienyl)(ethyl vinyl ether)iron tetrafluoroborate (1).

intermediate: Dicarbonyl(cyclopentadientyl)(trans‐3‐methyl‐2‐vinylcyclohexanone)iron tetrafluoroborate (3).

product: trans‐3‐Methyl‐2‐vinylcyclohexanone (4).
Ketones from Carboxylic Acids and
G
rignard Reagents: Methyl 6‐Oxodecanoate
Authors: Fujisawa Tamotsu , Sato Toshio
Published: November 2003

Ketones from carboxylic acids and Grignard reagents: methyl 6‐oxodecanoate

reactant: 6.92 g (0.052 mol) of 1‐chloro‐N,N,2‐trimethylpropenylamine

reactant: 8.01 g (0.050 mol) of adipic acid monomethyl ester

product: methyl 6‐oxodecanoate
Trisammonium Geranyl Diphosphate
Authors: Woodside Andrew B. , Huang Zheng , Poulter C. Dale
Published: November 2003

Trisammonium geranyl diphosphate

reactant: 1.54 g (10 mmol) of geraniol

intermediate: 0.83 g (4.8 mmol) of geranyl chloride

product: trisammonium geranyl diphosphate
(
R
)‐(+)‐ and (
S
)‐(−)‐2,2′‐Bis(Diphenylphosphino)‐1,1′‐Binaphthyl (BINAP)
Authors: Takaya Hidemasa , Akutagawa Susumu , Noyori Ryoji
Published: November 2003

(
R
)‐(+)‐ and (
S
)‐(−)‐2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl (BINAP)

intermediate: 2,2′‐Dibromo‐1,1′‐binaphthyl

intermediate: (±)‐2,2′‐Bis(diphenylphosphinyl)‐1,1′‐binaphthyl [(±)‐BINAPO]

intermediate: (
R
)‐(+)‐BINAPO

intermediate: 1 : 1 complex of (
S
)‐BINAPO and (−)‐DBT

intermediate: (
S
)‐BINAPO

intermediate: ((
R
)‐BINAPO and (−)‐DBT)

intermediate: (
R
)‐BINAPO‐(+)‐DBT‐complex

product: (
S
)‐BINAP
(
R
)‐(−)‐
N,N
‐Diethyl‐(
E
)‐Citronellalenamine and (
R
)‐(+)‐Citronellal via Isomerization of
N,N
‐Diethylgeranylamine or
N,N
‐Diethylnerylamine
Authors: Tani Kazuhide , Yamagata Tsuneaki , Otsuka Sei , Kumobayashi Hidenori , Akutagawa Susumu
Published: November 2003

(
R
)‐(−)‐
N,N
‐diethyl‐(
E
)‐citronellalenamine and (
R
)‐(+)‐citronellal via isomerization of
N,N
‐diethylgeranylamine or
N,N
‐diethylnerylamine

catalyst: [(+)‐2,2′‐Bis(diphenylphosphino)‐1,1′‐binaphthyl]‐(η
4
‐1,5‐cyclooctadiene) rhodium(I) perchlorate. [
Rh
{(+)‐BINAP} (1,5‐C
8
H
12
)] ClO
4

catalyst: [(−)‐2,2′‐Bis(diphenylphosphino)‐1,1′‐binaphthyl] (η
4
‐1,5‐cyclooctadiene) rhodium(I) perchlorate: [
Rh
{(−)‐BINAP}(1,5‐C
8
H
12
)] ClO
4

reactant: 83.8 g (0.40 mol) of
N,N
‐diethylgeranylamine

product: (
R
)‐(−)‐
N,N
‐diethyl‐(
E
)‐citronellalenamine

reactant: 83.8 g (0.40 mol) of
N,N
‐diethylnerylamine

product: (+)‐citronellal

catalyst: [Rh{(−)‐BINAP} (1,5‐C
8
H
12
)]ClO
4
THF

product: (
S
)‐(−)‐
N
‐cyclohexylcitronellalimine

product: (
R
)‐(−)‐
N,N
‐dimethyl‐3‐phenyl‐1(
E
)‐butenylamine
(−)‐Salsolidine
Authors: Meyers Albert I. , Boes Michael , Dickman Daniel A.
Published: November 2003

(−)‐Salsolidine

intermediate: 6,7‐Dimethoxy‐1,2,3,4‐tetrahydro‐2‐[(1‐tert‐butoxy‐3‐methyl)‐2‐butyliminomethyl]isoquinoline

reactant: 10.0 g (51.7 mmol) of 6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline 1

byproduct: valinol tert‐butyl ether

product: (S)‐6,7‐dimethoxy‐1‐methyl‐1,2,3,4‐tetrahydroisoquinoline (salsolidine)
α‐Diphenylmethylsilylation of Ester Enolates: 2‐Methyl‐2‐Undecene from Ethyl Decanoate
Authors: Larson Gerald L. , Lopez‐Cepero Ingrid Montes de , Mieles Luis Rodriguez
Published: November 2003

α‐Diphenylmethylsilylation of ester enolates: 2‐methyl‐2‐undecene from ethyl decanoate

reactant: 10.3 mL (11.6 g; 50 mmol) of diphenylmethylchlorosilane in 40 mL of tetrahydrofuran

intermediate: ethyl 2‐(diphenylmethylsilyl)decanoate

product: 2‐Methyl‐2‐undecene
N
‐Benzyl‐
N
‐methoxymethyl‐
N
‐(trimethylsilyl)methylamine as an Azomethine Ylide Equivalent: 2,6‐dioxo‐1‐phenyl‐4‐benzyl‐1,4‐diazabicyclo[3.3.0]octane
Authors: Padwa Albert , Dent William
Published: November 2003

N
‐benzyl‐
N
‐methoxymethyl‐
N
‐(trimethylsilyl)methylamine as an azomethine ylide equivalent: 2,6‐dioxo‐1‐phenyl‐4‐benzyl‐1,4‐diazabicyclo[3.3.0]octane

intermediate: N‐benzyl‐N‐(trimethylsilyl)methylamine

intermediate: N‐benzyl‐N‐methoxymethyl‐N‐(trimethylsilyl)methylamine

product: 2,6‐dioxo‐1‐phenyl‐4‐benzyl‐1,4‐diazabicyclo[3.3.0]octane
N
‐Acetyl‐
N
‐Phenylhydroxylamine via Catalytic Transfer Hydrogenation of Nitrobenzene Using Hydrazine and Rhodium on Carbon
Authors: Oxley P. W. , Adger B. M. , Sasse M. J. , Forth M. A.
Published: November 2003

N
‐acetyl‐
N
‐phenylhydroxylamine via catalytic transfer hydrogenation of nitrobenzene using hydrazine and rhodium on carbon

solvent: 100 mL of petroleum ether

product: N‐acetyl‐N‐phenylhydroxylamine
4‐Methoxy‐3‐penten‐2‐one
Authors: Kraus George A. , Krolski Michael E. , Sy James
Published: November 2003

4‐Methoxy‐3‐penten‐2‐one

product: 4‐methoxy‐3‐penten‐1‐one
(Phenylthio)nitromethane
Authors: Barrett Anthony G. M. , Dhanak Dashyant , Graboski Gregory G. , Taylor Sven J.
Published: November 2003

(Phenylthio)nitromethane

intermediate: phenylsulfenyl chloride

product: (phenylthio)nitromethane