bluuebunny/crossref_metadata_2025 huggingface dataset:
Dehydroxylation of Phenols; Hydrogenolysis of Phenolic Ethers: Biphenyl
Authors: Musliner Walter J. , Gates John W.
Published: November 2003

Dehydroxylation of phenols; hydrogenolysis of phenolic ethers: biphenyl

intermediate: 4‐(1‐phenyl‐5‐tetrazolyloxy)biphenyl

product: biphenyl
Mercury(II) Oxide‐Modified
H
unsdiecker Reaction: 1‐Bromo‐3‐chlorocyclobutane
Authors: Lampman Gary M. , Aumiller James C.
Published: November 2003

Mercury(II) oxide‐modified Hunsdiecker reaction: 1‐bromo‐3‐chlorocyclobutane

product: 1‐bromo‐3‐chlorocyclobutane
trans‐3‐Penten‐2‐one
Authors: Odom H. C. , Pinder A. R.
Published: November 2003

trans
‐3‐Penten‐2‐One

product: 3‐penten‐2‐one

byproduct: 4‐penten‐2‐one
2‐Acetyl‐1,3‐Cyclopentanedione
Authors: Merényi Ferenc , Nilsson Martin
Published: November 2003

2‐acetyl‐1,3‐cyclopentanedione

product: 2‐Acetyl‐3‐hydroxy‐2‐cyclopenten‐1‐one,

product: 1,3‐cyclopentanedione

product: 2‐acetyl‐4‐methyl‐1,3‐cyclopentanedione

product: 2‐acetyl‐4,4‐dimethyl‐1,3‐cyclopentanedione

product: 2‐acetyl‐5,5‐dimethyl‐1,3‐cyclohexanedione

product: 2‐acetyl‐1,3‐cycloheptanedione

product: 2‐acety‐1,3‐indanedione
Azoethane
Authors: Ohme Roland , Preuschhof Helmut , Heyne Hans‐Ulrich
Published: November 2003

Azoethane

intermediate:
N,N
′‐
Diethylsulfamide

product:
Azoethane

solvent: petroleum ether

intermediate:
N,N
′‐dicyclohexylsulfamide

intermediate:
N,N
′‐dispiro(cyclohexane‐1,9′‐fluorene)‐4‐ylsulfamide

product:
n
‐C
3
H
7

product:
n
‐C
4
H
9

product:
tert
‐C
4
H
9

product:
cyclo
‐C
6
H
11

product: 4‐NO
2
‐C
6
H
4
Diphenylketene
Authors: Taylor Edward C. , McKillop Alexander , Hawks George H.
Published: November 2003

Diphenylketene

reactant: 50.0 g. (0.236 mole) of diphenylacetic acid

intermediate: diphenylacetyl chloride

product: diphenylketene
The Formation and Alkylation of Specific Enolate Anions from an Unsymmetrical Ketone: 2‐Benzyl‐2‐methylcyclohexanone and 2‐benzyl‐6‐methylcyclohexanone
Authors: Gall Martin , House Herbert O.
Published: November 2003

The formation and alkylation of specific enolate anions from an unsymmetrical ketone: 2‐Benzyl‐2‐methylcyclohexanone and 2‐benzyl‐6‐methylcyclohexanone

intermediate: 2‐methyl‐1‐cyclohexen‐1‐yl acetate

reactant: 400 ml. of 1,2‐dimethoxyethane

reactant: 68.4 g. (0.400 mole) of freshly distilled benzyl bromide

product: 2‐benzyl‐2‐methylcyclohexanone

reactant: 21.0 g. (29.2 ml., 0.208 mole) of diisopropylamine

product: 2‐benzyl‐6‐methylcyclohexanone

reactant: 21–23 g.) and 3.74 g. (0.0505 mole) of ethyl formate

solvent: 2‐butanol

solvent:
p
‐xylene
(−)‐Isopinocampheol
Authors: Lane C. F. , Daniels J. J.
Published: November 2003

(−)‐Isopinocampheol

reactant: 27.2 g. (31.7 ml., 0.200 mole) of (+)‐α‐pinene

product: (−)‐isopinocampheol
Preparation and Reductive Cleavage of Enol Phosphates: 5‐Methylcoprost‐3‐ene
Authors: Muchmore D. C.
Published: November 2003

Preparation and reductive cleavage of enol phosphates: 5‐methylcoprost‐3‐ene

solvent: 4.0 ml. of triethylamine

reactant: 2.00 g. (0.0115 mole) of diethyl phosphorochloridate

byproduct: Ethylamine

intermediate: diethyl 5‐methylcoprost‐3‐en‐3‐yl phosphate

product: 5‐methylcoprost‐3‐ene

reactant: commercial grade of
tert
‐butyl alcohol

product: 3,4‐
seco
‐5‐methylcoprostan‐3,4‐dioic acid
Reduction of Ketones by use of the Tosylhydrazone Derivatives: Androstan‐17 β‐ol
Authors: Caglioti L.
Published: November 2003

Reduction of ketones by use of the tosylhydrazone derivatives: androstan‐17 β‐ol

product: 5α‐androstan‐17β‐ol
3‐Acetyl‐2,4‐Dimethylfuran
Authors: Howes P. D. , Stirling C. J. M.
Published: November 2003

3‐acetyl‐2,4‐dimethylfuran

intermediate:
Dimethyl‐2‐propynylsulfonium bromide

product: 3‐
Acetyl
‐2,4‐
dimethylfuran

reactant: 3‐Bromopropyne, supplied by British Drug Houses

reactant: Acetylacetone, supplied by British Drug Houses
Base‐Induced Rearrangement of Epoxides to Allylic Alcohols:
trans
‐Pinocarveol
Authors: Crandall J. K. , Crawley L. C.
Published: November 2003

Base‐induced rearrangement of epoxides to allylic alcohols:
trans
‐pinocarveol

reactant: 2.40 g. (0.0329 mole) of diethylamine

reactant: 5.00 g (0.0329 mole) of α‐pinene oxide

product:
trans
‐pinocarveol
Diazoacetophenone
Authors: Bridson John N. , Hooz John
Published: November 2003

Diazoacetophenone

reactant: Triethylamine (37.9 g., 52.1 ml., 0.375 mole)

reactant: 52.75 g. (43.56 ml., 0.3754 mole) of benzoyl chloride

byproduct: triethylamine hydrochloride

product: diazoacetophenone
Homogeneous Catalytic Hydrogenation: Dihydrocarvone
Authors: Ireland Robert E. , Bey P.
Published: November 2003

Homogeneous catalytic hydrogenation: dihydrocarvone

reactant: 10 g. (0.066 mole) of carvone

product: dihydrocarvone
Isoxazole Annelation Reaction: 1‐Methyl‐4,4a,5,6,7,8‐Hexahydronaphthalen‐2(3
H
)‐One
Authors: McMurry John E.
Published: November 2003

Isoxazole Annelation Reaction: 1‐Methyl‐4,4a,5,6,7,8‐Hexahydronaphthalen‐2(3
H
)‐ONE

intermediate: 3‐ethyl‐4‐hydroxymethyl‐5‐methylisoxazole

intermediate: 4‐chloromethyl‐3‐ethyl‐5‐methylisoxazole

intermediate: 2‐(3‐ethyl‐5‐methyl‐4‐isoxazolylmethyl)cyclohexanone

product: 1‐methyl‐4,4a,5,6,7,8‐hexahydronaphthalen‐2(3
H
)‐one
Reduction of Alkyl Halides and Tosylates with Sodium Cyanoborohydride in Hexamethylphosphoric Triamide (
HMPA
):
A
. 1‐Iododecane to
n
‐Decane
B
. 1‐Dodecyl Tosylate to
n
‐Dodecane
Authors: Hutchins Robert O. , Milewski Cynthia A. , Maryanoff Bruce E.
Published: November 2003

Reduction of alkyl halides and tosylates with sodium cyanoborohydride in hexamethylphosphoric triamide (HMPA): A. 1‐iododecane to
n
‐decane B. 1‐dodecyl tosylate to
n
‐dodecane

product:
n
‐decane

reactant: 1‐dodecyl tosylate (6.80 g., 0.0201 mole)

reactant: sodium cyanoborohydride (5.02 g., 0.0797 mole)

product:
n
‐dodecane
cis
‐α,β‐Unsaturated Acids: Isocrotonic Acid
Authors: Rappe C.
Published: November 2003

cis
‐α,β‐unsaturated acids: isocrotonic acid

intermediate: 1,3‐
Dibromo
‐2‐
butanone

product:
Isocrotonic acid

solvent: 25 ml. of petroleum ether

product: C
2
H
5

product:
n
‐C
3
H
7

product: 2‐C
3
H
7

product:
n
‐C
4
H
9

product:
tert
‐C
4
H
9

product:
n
‐C
5
H
11

product: (CH
3
)
2
CH(CH
2
)
2

product:
n
‐C
6
H
13
1,6‐Methano[10]Annulene
Authors: Vogel E. , Klug W. , Breuer A.
Published: November 2003

1,6‐Methano[10]Annulene

intermediate: 1,4,5,8‐
Tetrahydronaphthalene
(
isotetralin
)

intermediate: 11,11‐
Dichlorotricyclo
[4.4.1.0
1,6
]
undeca
‐3,8‐
diene

intermediate:
Tricyclo
[4.4.1.0
1,6
]
undeca
‐3,8‐
diene

product: 1,6‐
Methano
[10]
annulene

intermediate: 2,3‐dichloro‐5,6‐dicyanohydroquinone
γ‐Hydroxy‐α,β‐Unsaturated Aldehydes
via
1,3‐Bis(Methylthio)Allyllithium:
trans
‐4‐Hydroxy‐2‐Hexenal
Authors: Erickson Bruce W.
Published: November 2003

γ‐hydroxy‐α,β‐unsaturated aldehydes
via
1,3‐bis(methylthio)allyllithium:
trans
‐4‐hydroxy‐2‐hexenal

reactant: 50 g. (56 ml., 1.0 mole) of methanethiol

intermediate: 1,3‐bis(methylthio)‐2‐propanol

solvent: 100‐ml. portions of hexane

intermediate: 1,3‐bis(methylthio)‐2‐methoxypropane

intermediate: 1,3‐bis(methylthio)‐1‐hexen‐4‐ol

product:
trans
‐4‐hydroxy‐2‐hexenal

byproduct: 2,4‐dinitrophenylhydrazone

byproduct: 1,3‐bis(methylthio)propene

byproduct: 1,3‐bis(methylthio)‐1‐butene
Cyclopropyldiphenylsulfonium Tetrafluoroborate
Authors: Bogdanowicz Mitchell J. , Trost Barry M.
Published: November 2003

Cyclopropyldiphenylsulfonium tetrafluoroborate

reactant: 347 g. (1.70 mole) of 1‐chloro‐3‐iodopropane

intermediate: 118.7 g. (0.3386 mole) of 3‐chloropropyldiphenylsulfonium tetrafluoroborate

reactant: 15 g. of sodium tetrafluoroborate

product: cyclopropyldiphenylsulfonium tetrafluoroborate
2,2‐(Ethylenedithio)Cyclohexanone
Authors: Woodward R. B. , Pachter I. J. , Scheinbaum M. L.
Published: November 2003

2,2‐(Ethylenedithio)cyclohexanone

reactant: 10 g. (0.025 mole) of ethylene dithiotosylate

product: 2,2‐(ethylenedithio)cyclohexanone
Geranyl Chloride
Authors: Calzada Jose G. , Hooz John
Published: November 2003

Geranyl chloride

reactant: 15.42 g. of geraniol (0.1001 mole)

reactant: 34.09 g. (0.1301 mole) of triphenylphosphine

product: geranyl chloride

product:
n
‐pentyl bromide

product: benzyl bromide

product: Farnesyl bromide
Cyclobutanone
via
Solvolytic Cyclization
Authors: Hanack M. , Dehesch T. , Hummel K. , Nierth A.
Published: November 2003

Cyclobutanone
via
solvolytic cyclization

reactant: 75 g. (0.27 mole) of trifluoromethanesulfonic anhydride

reactant: 15 g. (0.21 mole) of 3‐butyn‐1‐ol

reactant: 11.5 g. (0.0846 mole) of sodium trifluoroacetate

intermediate: 17 g. (0.084 mole) of 3‐butyn‐1‐yl trifluoromethanesulfonate

product: cyclobutanone
Benzocyclopropene
Authors: Billups W. E. , Blakeney A. J. , Chow W. Y.
Published: November 2003

Benzocyclopropene

intermediate: 7,7‐
Dichlorobicyclo
[4.1.0]
hept
‐3‐
ene

product:
Benzocyclopropene
Bicyclo[2.1.0]pent‐2‐ene
Authors: Andrist A. Harry , Baldwin John E. , Pinschmidt Robert K.
Published: November 2003

Bicyclo[2.1.0]pent‐2‐ene
1‐Bromo‐3‐methyl‐2‐butanone
Authors: Gaudry M. , Marquet A.
Published: November 2003

1‐Bromo‐3‐methyl‐2‐butanone

product: 95% of 1‐bromo‐3‐methyl‐2‐butanone

byproduct: 3‐bromo‐3‐methyl‐2‐butanone
2‐Bromohexanoyl Chloride
Authors: Harpp David N. , Bao L. Q. , Coyle Christopher , Gleason John G. , Horovitch Sharon
Published: November 2003

2‐Bromohexanoyl chloride

product: 2‐bromohexanoyl chloride

product: 2‐bromohexanoic acid
Cyclobutadiene in Synthesis:
endo
‐Tricyclo[4.4.0.0
2,5
]deca‐3,8‐diene‐7,10‐dione
Authors: Brener L. , McKennis J. S. , Pettit R.
Published: November 2003

Cyclobutadiene in synthesis:
endo
‐tricyclo[4.4.0.0
2,5
]deca‐3,8‐diene‐7,10‐dione

product:
endo
‐tricyclo[4.4.0.0
2,5
]deca‐3‐8‐dien‐7,10‐dione
6,7‐Dimethoxy‐3‐Isochromanone
Authors: Finkelstein J. , Brossi A.
Published: November 2003

6,7‐Dimethoxy‐3‐isochromanone

reactant: 49.0 g. (0.250 mole) of 3,4‐dimethoxyphenylacetic acid

product: 6,7‐dimethoxy‐3‐isochromanone
Oxidation with the Chromium Trioxide–Pyridine Complex Prepared
in situ:
1‐Decanal
Authors: Ratcliffe R. W.
Published: November 2003

Oxidation with the chromium trioxide–pyridine complex prepared
in situ:
1‐Decanal

product: 1‐decanal
Phase‐Transfer
H
ofmann Carbylamine Reaction:
tert
‐Butyl Isocyanide
Authors: Gokel George W. , Widera Ronald P. , Weber William P.
Published: November 2003

Phase‐transfer Hofmann carbylamine reaction:
tert
‐butyl isocyanide

product:
tert
‐butyl isocyanide

CH
3
(CH
2
)
2
CH
2


C
6
H
5
CH
2


CH
3
(CH
2
)
10
CH
2


cyclo‐C
6
H
11


C
6
H
5


CH
3


CH
3
CH
2

5‐Acetyl‐1,2,3,4,5‐Pentamethylcyclopentadiene
Authors: King R. B. , Douglas W. M. , Efraty A.
Published: November 2003

5‐acetyl‐1,2,3,4,5‐pentamethylcyclopentadiene

product: 5‐acetyl‐1,2,3,4,5‐pentamethylcyclopentadiene
Allylic Oxidation with Hydrogen Peroxide–Selenium Dioxide:
trans
‐Pinocarveol
Authors: Coxon J. M. , Dansted E. , Hartshorn M. P.
Published: November 2003

Allylic oxidation with hydrogen peroxide–selenium dioxide:
trans
‐pinocarveol

reactant: 68 g. (0.50 mole) of β‐pinene

product:
trans
‐Pinocarveol
5,6‐Dihydro‐2
H
‐Pyran‐2‐one and 2
H
‐Pyran‐2‐one
Authors: Nakagawa M. , Saegusa J. , Tonozuka M. , Obi M. , Kiuchi M. , Hino T. , Ban Y.
Published: November 2003

5,6‐Dihydro‐2
H
‐Pyran‐2‐one and 2
H
‐Pyran‐2‐one

product: 5,6‐dihydro‐2
H
‐pyran‐2‐one

reactant: 18.6 g. (0.105 mole) of
N
‐bromosuccinimide

product: 2
H
‐pyran‐2‐one
Enone Reduction‐Enolate Alkylation Sequence: 2‐Allyl‐3‐Methylcyclohexanone
Authors: Caine Drury , Chao Sam T. , Smith Homer A.
Published: November 2003

Enone reduction‐enolate alkylation sequence: 2‐allyl‐3‐methylcyclohexanone

byproduct: 3‐methylcyclohexanone

product: 2‐allyl‐3‐methylcyclohexanone

reactant: 3‐Methyl‐2‐cyclohexen‐1‐one, b.p. 76–78° (11 mm.), was purchased from Aldrich Chemical Company, Inc.

reactant: Allyl bromide purchased from Eastman Organic Chemicals, Inc.
trans
‐Iodopropenylation of Alkyl Halides: (
E
)‐1‐Iodo‐4‐Phenyl‐2‐Butene
Authors: Hirai Koichi , Kishida Yukichi
Published: November 2003

trans
‐Iodopropenylation of alkyl halides: (
E
)‐1‐iodo‐4‐phenyl‐2‐butene

intermediate: 4,5‐
Dihydro
‐2‐(2‐
propenylthio
)
thiazole

intermediate: 4,5‐
Dihydro
‐2‐[(1‐
phenylmethyl
‐2‐
propenyl
)
thio
]
thiazole

reactant: 2.15 g. (0.0125 mole) of benzyl bromide

product: (E)‐1‐
Iodo
‐4‐
phenyl
‐2‐
butene

intermediate:
N
‐Methyl‐2‐methylthiothiazolium iodide

product: triphenylphosphonium salt

product: (4‐methoxyphenyl‐2‐butenyl)triphenylphosphonium iodide

product: (2‐octenyl)triphenylphosphonium iodide

product: (2‐octadecenyl)triphenylphosphonium iodide
Methyl Groups by Reduction of Aromatic Carboxylic Acids with Trichlorosilane‐ Tri‐
n
‐Propylamine: 2‐Methylbiphenyl
Authors: Li George S. , Ehler David F. , Benkeser R. A.
Published: November 2003

Methyl groups by reduction of aromatic carboxylic acids with trichlorosilane‐ tri‐
n
‐propylamine: 2‐methylbiphenyl

product: 2‐methylbiphenyl

product: Toluene

product:
m
‐Xylene

product:
p
‐Xylene

product: Mesitylene

product:
p
‐Chlorotoluene

product:
p
‐Bromotoluene

product:
o
‐Xylene
Ring Contraction
via
a
F
avorskii‐Type Rearrangement: Cycloundecanone
Authors: Wohllebe J. , Garbisch E. W.
Published: November 2003

Ring contraction
via
a Favorskii‐type rearrangement: cycloundecanone

intermediate: methyl 1‐cycloundecenecarboxylate

product: cycloundecanone
Selective Epoxidation of Terminal Double Bonds: 10,11‐Epoxyfarnesyl Acetate
Authors: Hanzlik R. P.
Published: November 2003

Selective epoxidation of terminal double bonds: 10,11‐epoxyfarnesyl acetate

intermediate:
Farnesyl acetate

solvent: 100‐ml. portions of petroleum ether

intermediate: 10‐
Bromo
‐11‐
hydroxy
‐10,11‐
dihydrofarnesyl acetate

product: 10,11‐
Epoxyfarnesyl acetate
Cuprous Ion‐Catalyzed Oxidative Cleavage of Aromatic
o
‐Diamines by Oxygen: (
Z,Z
)‐2,4‐Hexadienedinitrile
Authors: Tsuji Jiro , Takayanagi Hiroshi
Published: November 2003

Cuprous ion‐catalyzed oxidative cleavage of aromatic
o
‐diamines by oxygen: (
Z,Z
)‐2,4‐hexadienedinitrile

product: (
Z,Z
)‐2,4‐hexadienedinitrile
Diethylaminosulfur Trifluoride
Authors: Middleton W. J. , Bingham E. M.
Published: November 2003

Diethylaminosulfur trifluoride

reactant: 145 g. (1.00 mole) of
N,N
‐diethylaminotrimethylsilane

byproduct: fluorotrimethylsilane

product: diethylaminosulfur trifluoride
1,2‐Dimethylcyclobutenes by Reductive Ring‐Contraction of Sulfolanes:
cis
‐7,8‐Dimethylbicyclo[4.2.0]oct‐7‐ene
Authors: Photis James M. , Paquette Leo A.
Published: November 2003

1,2‐Dimethylcyclobutenes by reductive ring‐contraction of sulfolanes:
cis
‐7,8‐dimethylbicyclo[4.2.0]oct‐7‐ene

intermediate:
cis
‐1,2‐cyclohexanedimethanol

intermediate: cis‐8‐
Thiabicyclo
[4.3.0]
nonane.

intermediate: 95 g. (0.32 mole) of
cis
‐1,2‐cyclohexanedimethanol dimethanesulfonate

intermediate: cis‐8‐
Thiabicyclo
[4.3.0]
nonane
8,8‐
dioxide
[
benzo
[c]
thiophene
2,2‐
dioxide
, cis‐
octahydro
‐]

intermediate: 7,9‐
Dimethyl
‐cis‐8‐
thiabicyclo
[4.3.0]
nonane
8,8‐
dioxide.

product: cis‐7,8‐
Dimethylbicyclo
[4.2.0]
oct
‐7‐
ene.
Dimethyl Nitrosuccinate
Authors: Zen S. , Kaji E.
Published: November 2003

Dimethyl nitrosuccinate

solvent: 500 ml. of anhydrous
N,N
‐dimethylacetamide

product: dimethyl nitrosuccinate

product: dimethyl 2‐nitropentanedioate
Dimethyl 2,3‐Pentadienedioate
Authors: Bryson T. A. , Dolak T. M.
Published: November 2003

Dimethyl 2,3‐Pentadienedioate

reactant: 60.0 g. (0.297 mole) of diethyl acetone‐1,3‐dicarboxylate

intermediate: dimethyl 3‐chloro‐2‐pentenedioate

product: dimethyl 2,3‐pentadienedioate
Tricarbonyl[(2,3,4,5‐η)‐2,4‐Cyclohexadien‐1‐One]Iron and Tricarbonyl[(1,2,3,4,5‐η)‐2‐Methoxy‐2,4‐Cyclohexadien‐1‐yl]Iron(1+) Hexafluorophosphate(1−) from Anisole
Authors: Birch A. J. , Chamberlain K. B.
Published: November 2003

Tricarbonyl[(2,3,4,5‐η)‐2,4‐cyclohexadien‐1‐one]iron and tricarbonyl[(1,2,3,4,5‐η)‐2‐methoxy‐2,4‐cyclohexadien‐1‐yl]iron(1+) hexafluorophosphate(1−) from anisole

reactant: 50 g. (0.46 mole) of anisole

solvent: 100‐ml. portions of petroleum ether

intermediate: 1‐methoxy‐1,4‐cyclohexadiene

intermediate:
Tricarbonyl
[(1,2,3,4‐η)‐1‐
and
2‐
methoxy
‐1,3‐
cyclohexadiene]iron.

intermediate:
Tricarbonyl
[(1,2,3,4,5‐η)‐1‐
and
2‐
methoxy
‐2,4‐
cyclohexadien
‐1‐
yl
]
iron
(1+)
tetrafluoroborate
(1−)

reactant: Triphenylmethyl tetrafluoroborate (34 g., 0.10 mole)

product:
Tricarbonyl
[(2,3,4,5‐η)‐2,4‐
cyclohexadian
‐1‐
one
]
iron.

product:
Tricarbonyl
[(1,2,3,4,5‐η)‐2‐
methoxy
‐2,4‐
cyclohexadien
‐1‐
yl
]
iron
(1+)
hexafluorophosphate
(1−)

product: diphenylamine
3‐Alkyl‐1‐Alkynes Synthesis: 3‐Ethyl‐1‐Hexyne
Authors: Quillinan A. J. , Scheinmann F.
Published: November 2003

3‐Alkyl‐1‐alkynes synthesis: 3‐ethyl‐1‐hexyne

solvent: 400 ml. of pure, dry pentane

product: 3‐ethyl‐1‐hexyne

product: 3‐ethylhexane
Bicyclic Ketones for the Synthesis of Tropinoids: 2α,4α‐Dimethyl‐8‐Oxabicyclo[3.2.1]oct‐6‐en‐3‐one
Authors: Ashcroft M. R. , Hoffmann H. M. R.
Published: November 2003

Bicyclic ketones for the synthesis of tropinoids: 2α,4α‐dimethyl‐8‐oxabicyclo[3.2.1]oct‐6‐en‐3‐one

intermediate: 2,4‐
Dibromo
‐3‐
pentanone
(1)

reactant: 28 g. (30 ml., 0.41 mole) of freshly‐distilled furan

product: 2α,4α‐dimethyl‐8‐oxabicyclo[3.2.1]oct‐6‐en‐3‐one (2)
2,3‐Dicyanobutadiene as a Reactive Intermediate byin situGeneration from 1,2‐Dicyanocyclobutene: 2,3‐Dicyano‐1,4,4a,9a‐Tetrahydrofluorene
Authors: Belluš D. , Sauter H. , Weis C. D.
Published: November 2003

2,3‐Dicyanobutadiene as a reactive intermediate byin situgeneration from 1,2‐dicyanocyclobutene: 2,3‐dicyano‐1,4,4a,9a‐tetrahydrofluorene

intermediate: 1‐Chloro‐1,2‐dicyanocyclobutane(1)

intermediate: 1,2‐Dicyanocyclobutene(2)

reactant: 131 g. (1.30 moles) of triethylamine

product: 2,3‐Dicyano‐1,4,4a,9a‐tetrahydrofluorene(3)

reactant: 23.3 g. (0.201 mole) of indene

product: 2,3‐dicyanofluorene

product: 4,5‐Dicyanotricyclo‐[6.2.1.02,7]undeca‐4,9‐diene

product: 8,9‐Dicyano‐6b,7,10,10a‐tetrahydrofluoranthene

product: 3,4‐Dicyanobicyclo[4.3.0]non‐3‐ene

product: 1,2‐Dicyanocyclohexene

product: 1,2‐Dicyano‐4,5‐diphenylcyclohexene

product: 1,2‐Dicyano‐4‐butoxycyclohexene

product: 1,2‐Dicyano‐4,5‐trans‐dichlorocyclohexene

product: 1,2‐Dicyano‐4‐(2 ‐pyridyl)cyclohexene
Fluorinations with Pyridinium Polyhydrogen Fluoride Reagent: 1‐Fluoroadamantane
Authors: Olah George A. , Watkins Michael
Published: November 2003

Fluorinations with pyridinium polyhydrogen fluoride reagent: 1‐fluoroadamantane

product: 1‐fluoroadamantane

product: Isopropyl

product:
sec
‐Butyl

product:
tert
‐Butyl

product: 3‐Ethyl‐3‐fluoropentane

product: 3‐Fluoro‐3‐methylheptane

product: 4‐Fluoro‐3‐methylheptane

product: Cyclohexyl fluoride

product: 2‐Fluoronorbornane

product: 2‐Fluoroadamantane

product: 1‐Fluoro‐1‐phenylethane

product: Isopropyl fluoride

product:
n
‐Propyl fluoride

product:
sec
‐Butyl fluoride

product:
tert
‐Butyl fluoride

product: Cyclopentyl fluoride

product: Cyclohexyl fluoride

product: Cycloheptyl fluoride

product: 2‐Fluoronorbornane

product: 2,2‐Difluorohexane

product: 3,3‐Difluorohexane
Phosphine–Nickel Complex Catalyzed Cross‐Coupling of
G
rignard Reagents with Aryl and Alkenyl Halides: 1,2‐Dibutylbenzene
Authors: Kumada Makoto , Tamao Kohei , Sumitani Koji
Published: November 2003

Phosphine–nickel complex catalyzed cross‐coupling of Grignard reagents with aryl and alkenyl halides: 1,2‐Dibutylbenzene

byproduct: 1‐butyl‐2‐chlorobenzene

product: 1,2‐dibutylbenzene

product: C
6
H
5
C
4
H
9

product: 1,3‐[1,3‐[(CH
3
)
3
SiCH
2
]
2
C
6
H
4

product: (CH
3
)
2
CH‐ and CH
3
(CH
2
)
2
C
6
H
5

product: (
S
)‐(+)‐C
6
H
5
CH(CH
3
)CHCH
2

product: (
Z
)‐C
6
H
5
CHCHC
6
H
5

product: (
Z
)‐C
6
H
5
CHCHC
6
H
5

product: 4‐ClC
6
H
4
CHCH
2

product: α‐C
10
H
7
C(CH
3
)CH
2
Sulfide Synthesis in Preparation of Unsymmetrical Dialkyl Disulfides:
sec
‐Butyl Isopropyl Disulfide
Authors: Alonso M. E. , Aragona H.
Published: November 2003

Sulfide synthesis in preparation of unsymmetrical dialkyl disulfides:
sec
‐butyl isopropyl disulfide

product: sec‐
Butyl isopropyl disulfide
(3).
1‐
N
‐Acylamino‐1,3‐dienes from 2,4‐Pentadienoic Acids by the
C
urtius Rearrangement: Benzyl
trans
‐1,3‐butadiene‐1‐carbamate
Authors: Jessup Peter J. , Petty C. Bruce , Roos Jan , Overman Larry E.
Published: November 2003

1‐
N
‐Acylamino‐1,3‐dienes from 2,4‐pentadienoic acids by the Curtius rearrangement: Benzyl
trans
‐1,3‐butadiene‐1‐carbamate

intermediate: trans‐2,4‐
Pentadienoic acid

product:
Benzyl
trans‐1,3‐
butadiene
‐1‐
carbamate

reactant: Acrolein contaminated by 3% water was obtained by the submitters from Aldrich Chemical Company, Inc.

reactant:
N,N
‐Diisopropylethylamine was supplied by Aldrich Chemical Company, Inc.

reactant: Ethyl chloroformate obtained from Aldrich Chemical Company, Inc.

reactant: Reagent grade benzyl alcohol
Bromohydrins from Alkenes and
N
‐Bromosuccinimide in Dimethyl Sulfoxide:
erythro
‐2‐Bromo‐1,2‐diphenylethanol
Authors: Langman A. W. , Dalton D. R.
Published: November 2003

Bromohydrins from alkenes and
N
‐bromosuccinimide in dimethyl sulfoxide:
erythro
‐2‐bromo‐1,2‐diphenylethanol

reactant: 18.0 g. (0.100 mole) of (
E
)‐stilbene

product:
erythro
‐2‐bromo‐1,2‐diphenylethanol

solvent: 600 ml. of petroleum ether

product:
threo
‐C
6
H
5
CH(OH)CH(Br)C
6
H
5

product:
erythro
‐C
6
H
5
CH(OH)CH(Br)CH
3

product:
threo
‐C
6
H
5
CH(OH)CH(Br)CH
3

product: C
6
H
5
CH(OH)CH
2
Br

product: C
6
H
5
C(CH
3
)(OH)CH
2
Br

product: C
6
H
5
CH
2
CH(OH)CH
2
Br

product:
erythro
‐(CH
3
)
3
CCH(Br)CH(OH)CH
3

product:
threo
‐(CH
3
)
3
CCH(Br)CH(OH)CH
3

product: (CH
3
)
3
CCH(Br)CH
2
OH

product: (CH
3
)
3
CC(CH
3
)(OH)CH
2
Br
α‐Chlorination of Carboxylic Acids Mediated by Chlorosulfonic Acid: ε‐Benzoylamino‐α‐chlorocaproic Acid
Authors: Ogata Yoshiro , Sugimoto Toshiyuki , Inaishi Morio
Published: November 2003

α‐Chlorination of carboxylic acids mediated by chlorosulfonic acid: ε‐benzoylamino‐α‐chlorocaproic acid

product: ε‐benzoylamino‐α‐chlorocaproic acid

reactant: Chlorosulfonic acid
α‐Chloro Enamines, Reactive Intermediates for Synthesis: 1‐Chloro‐
N,N
,2‐Trimethylpropenylamine
Authors: Haveaux B. , Dekoker A. , Rens M. , Sidani A. R. , Toye J. , Ghosez L.
Published: November 2003

α‐Chloro Enamines, Reactive Intermediates for Synthesis: 1‐Chloro‐
N,N
,2‐Trimethylpropenylamine

reactant: 115 g. (1.00 mole) of freshly distilled
N,N
‐dimethylisobutyramide

solvent: 150 ml. of dry, low‐boiling petroleum ether

product: 1‐chloro‐
N,N
,2‐trimethylpropenylamine
Conversion of Esters to Amides with Dimethylaluminum Amides:
N,N
‐Dimethylcyclohexanecarboxamide
Authors: Lipton Michael F. , Basha Anwer , Weinreb Steven M.
Published: November 2003

Conversion of esters to amides with dimethylaluminum amides:
N,N
‐dimethylcyclohexanecarboxamide

reactant: 7.10 g. (0.0500 mole) of methyl cyclohexanecarboxylate

product:
N,N
‐dimethylcyclohexanecarboxamide
Glutaconaldehyde Sodium Salt from Hydrolysis of Pyridinium‐1‐Sulfonate
Authors: Becher Jan
Published: November 2003

Glutaconaldehyde sodium salt from hydrolysis of pyridinium‐1‐sulfonate

product: glutaconaldehyde sodium salt dihydrate

product: glutaconaldehyde potassium salt

product: glutaconaldehyde tetrabutylammonium salt monohydrate
A New Reagent for
tert
‐Butoxycarbonylation: 2‐
tert
‐Butoxycarbonyloxyimino‐2‐phenylacetonitrile
Authors: Itoh Masumi , Hagiwara Daijiro , Kamiya Takashi
Published: November 2003

A new reagent for
tert
‐butoxycarbonylation: 2‐
tert
‐butoxycarbonyloxyimino‐2‐phenylacetonitrile

intermediate: 2‐hydroxyimino‐2‐phenylacetonitrile

product: 2‐
tert
‐butoxycarbonyloxyimino‐2‐phenylacetonitrile

C
6
H
5
CH
2


4‐CH
3
OC
6
H
4
CH
2


Cl
3
CCH
2

PhotochemicalRing Contraction of 2‐Ethoxypyrrolin‐5‐ones to Cyclopropanone Derivatives:
tert
‐Butyl
N
‐(1‐Ethoxycyclopropyl)carbamate
Authors: Crockett Geoffrey C. , Koch Tad H.
Published: November 2003

Photochemical ring contraction of 2‐ethoxypyrrolin‐5‐ones to cyclopropanone derivatives:
tert
‐butyl
N
‐(1‐ethoxycyclopropyl)carbamate

intermediate: silver salt of succinimide

intermediate: 6.26 g. (0.0493 mole) of redistilled 2‐ethoxypyrrolin‐5‐one

product:
tert
‐butyl
N
‐(1‐ethoxycyclopropyl)carbamate
Regioselective Mannich Condensation with Dimethyl(Methylene)Ammonium Trifluoroacetate: 1‐(Dimethylamino)‐4‐Methyl‐3‐Pentanone
Authors: Gaudry Michel , Jasor Yves , Khac Trung Bui
Published: November 2003

Regioselective mannich condensation with dimethyl(methylene)ammonium trifluoroacetate: 1‐(dimethylamino)‐4‐methyl‐3‐pentanone

intermediate: bis(dimethylamino)methane

product: 1‐(dimethylamino)‐4‐methyl‐3‐pentanone
Removal of
N
α
‐Benzyloxycarbonyl Groups from Sulfur‐Containing Peptides by Catalytic Hydrogenation in Liquid Ammonia:
O
‐
tert
‐Butyl‐
L
‐Seryl‐
S
‐
tert
‐Butyl‐
L
‐Cysteine
tert
‐Butyl Ester
Authors: Felix Arthur M. , Jimenz Manuel H. , Meienhofer Johannes
Published: November 2003

Removal of
N
α
‐benzyloxycarbonyl groups from sulfur‐containing peptides by catalytic hydrogenation in liquid ammonia:
O
‐
tert
‐butyl‐
L
‐seryl‐
S
‐
tert
‐butyl‐
L
‐cysteine
tert
‐butyl ester

intermediate:
L
‐
Methionine.

product: O‐tert‐
Butyl
‐
L
‐
seryl
‐S‐tert‐
butyl
‐
L
‐
cysteine
tert‐
butyl ester

solvent: petroleum ether

reactant:
S
‐
tert
‐Butyl‐
L
‐cysteine
tert
‐butyl ester

solvent: ethyl acetate–petroleum ether
Vinyl Sulfides from Thioacetals with Copper(I) Trifluoromethanesulfonate: (
Z
)‐2‐Methoxy‐1‐Phenylthio‐1,3‐Butadiene
Authors: Cohen Theodore , Ruffner Robert J. , Shull David W. , Fogel Elaine R. , Falck J. R.
Published: November 2003

Vinyl sulfides from thioacetals with copper(I) trifluoromethanesulfonate: (
Z
)‐2‐methoxy‐1‐phenylthio‐1,3‐butadiene

intermediate:
Bis(phenylthio)methane

intermediate: 4,4‐
Bis(phenylthio)
‐3‐
methoxy
‐1‐
butene

product: (Z)‐2‐
Methoxy
‐1‐
phenylthio
‐1,3‐
butadiene

reactant: 3.27 g. [0.00650 mole, 0.0126 g.‐atom of copper(I)] of bis[copper(I) trifluoromethanesulfonate] benzene complex

reactant: Thiophenol was purchased from Aldrich Chemical Company, Inc.

reactant: Acrolein was purchased by the submitters from Cationics, Division of Columbia Organic Chemicals Company, Inc. (Columbia, South Carolina)
Atropaldehyde
Authors: Crossland Ingolf
Published: November 2003

Atropaldehyde

intermediate: dichlorophenylcyclopropane

intermediate: Atropaldehyde diethyl acetal

product: atropaldehyde
Cyclobutanone
Authors: Krumpolc Miroslav , Rocek Jan
Published: November 2003

Cyclobutanone

intermediate: cyclobutanol

product: cyclobutanone

solvent: 200‐mL portions of methylene chloride

byproduct: 3‐butene‐1‐ol

byproduct: 4‐hydroxybutyraldehyde
Deoxygenation of Epoxides with Lower Valent Tungsten Halides:
trans
‐Cyclododecene
Authors: Umbreit Martha A. , Sharpless K. Barry
Published: November 2003

Deoxygenation of epoxides with lower valent tungsten halides:
trans
‐cyclododecene

product:
trans
‐cyclododecene
2,6‐Di‐
tert
‐Butyl‐4‐Methylpyridine
Authors: Anderson Albert G. , Stang Peter J.
Published: November 2003

2,6‐Di‐
tert
‐butyl‐4‐methylpyridine

intermediate: 2,6‐di‐
tert
‐butyl‐4‐methylpyrylium trifluoromethanesulfonate

product: 2,6‐Di‐
tert
‐butyl‐4‐methylpyridine
Diels‐Alder Reaction of 1,2,4,5‐Hexatetraene: Tetramethyl[2.2]paracyclophane‐4,5,12,13‐tetracarboxylate
Authors: Hopf Henning , Böhm Ingrid , Kleinschroth Jürgen
Published: November 2003

Diels‐Alder reaction of 1,2,4,5‐hexatetraene: Tetramethyl[2.2]paracyclophane‐4,5,12,13‐tetracarboxylate

intermediate: 1,2,4,5‐hexatetraene

reactant: 69.4 g (60 mL, 0.49 mol) of dimethyl acetylenedicarboxylate

product: tetramethyl[2.2]paracyclophane‐4,5,12,13‐tetracarboxylate
N
‐(2,4‐Diformyl‐5‐Hydroxyphenyl)Acetamide
Authors: Hocker Jürgen , Giesecke Henning
Published: November 2003

N
‐(2,4‐diformyl‐5‐hydroxyphenyl)acetamide

intermediate:
N
‐[2,4‐bis(1,3‐diphenylimidazolidin‐2‐yl)‐5‐hydroxyphenyl]acetamide

product:
N
‐(2,4‐diformyl‐5‐hydroxyphenyl)acetamide

product: 3‐Methylimidazole‐5‐carboxaldehyde

product: 2‐phenylindole‐3‐carboxaldehyde

product: 4‐Hydroxybenzaldehyde

product: 4‐Hydroxy‐3,5‐dimethylbenzaldehyde

product: 3‐Cyclohexyl‐5‐methylsalicyladehyde

product: 4‐Dimethylamino‐5‐methylsalicylaldehyde

product: 4‐Dimethylaminosalicylaldehyde

product: Resorcinol‐2,4,6‐tricarboxaldehyde

product: 4‐Hydroxy‐5‐methoxyisophthalaldehyde

product: 4‐Hydroxy‐6‐methoxyisophthalaldehyde

product: Pyrogallol‐4,6‐dicarboxaldehyde

product: 8‐Hydroxyquinoline‐7‐carboxaldehyde
Preparation of Chlorophenyldiazirine and Thermal Generation of Chlorophenyl Carbene: 1,2‐Diphenyl‐3‐methylcyclopropene
Authors: Padwa Albert , Pulwer Mitchell J. , Blacklock Thomas J.
Published: November 2003

Preparation of chlorophenyldiazirine and thermal generation of chlorophenyl carbene: 1,2‐diphenyl‐3‐methylcyclopropene

product: 1‐chloro‐1,2‐diphenyl‐3‐methylcyclopropanes

product: 1,2‐diphenyl‐3‐methylcyclopropene

product: phenylchlorodiazirine

product: (
S
)‐1‐chloro‐(
S,S
)‐1,2‐diphenyl‐(
R
)‐3‐methylcyclopropane

product: (
S
)‐1‐chloro‐(
S,R
)‐1,2‐diphenyl‐(
S
)‐3‐methylcyclopropane
Electrohydrodimerization of an Activated Alkene: Tetraethyl 1,2,3,4‐Butanetetracarboxylate
Authors: White D. A.
Published: November 2003

Electrohydrodimerization of an activated alkene: tetraethyl 1,2,3,4‐butanetetracarboxylate

product: Tetraethyl 1,2,3,4‐butanetetracarboxylate
Epoxidation of Olefins by Hydrogen Peroxide‐Acetonitrile:
cis
‐Cyclooctene Oxide
Authors: Bach R. D. , Knight J. W.
Published: November 2003

Epoxidation of olefins by hydrogen peroxide‐acetonitrile:
cis
‐cyclooctene oxide

product:
cis
‐cyclooctene oxide
Reduction of Ketones to Hydrocarbons with Triethylsilane:
m
‐Nitroethylbenzene
Authors: Fry James L. , Silverman Steven B. , Orfanopoulos Michael
Published: November 2003

Reduction of ketones to hydrocarbons with triethylsilane:
m
‐nitroethylbenzene

reactant: 20.9 g (0.180 mol) of triethylsilane

reactant: 10.0 g (0.0606 mol) of m‐nitroacetophenone

product: m‐nitroethylbenzene
Synthesis of 1,4‐Diketones from Silyl Enol Ethers and Nitroolefins: 2‐(2‐Oxopropyl)Cyclohexanone
Authors: Miyashita Masaaki , Yanami Tetsuji , Yoshikoshi Akira
Published: November 2003

Synthesis of 1,4‐diketones from silyl enol ethers and nitroolefins: 2‐(2‐Oxopropyl)cyclohexanone

reactant: 40 mL (34 g, 0.20 mol) of 1‐trimethylsiloxy‐1‐cyclohexene

product: 2‐(2‐oxopropyl)cyclohexanone
m
‐Trifluoromethylbenzenesulfonyl Chloride
Authors: Hoffman R. V.
Published: November 2003

m
‐trifluoromethylbenzenesulfonyl chloride

product:
m
‐trifluoromethylbenzenesulfonyl chloride

unknown:
m
‐CF
3

unknown:
p
‐NO
2

unknown:
m
‐NO
2

unknown:
p
‐Cl

unknown:
p
‐CO
2
CH
3

unknown: 3,5‐di‐NO
2

unknown:
m
‐CH
3

unknown: H

unknown:
p
‐OCH
3
Bis(2,2,2‐Trichloroethyl) Azodicarboxylate
Authors: Little R. Daniel , Venegas Manuel G.
Published: November 2003

Bis(2,2,2‐trichloroethyl) azodicarboxylate

intermediate: bis(2,2,2‐trichloroethyl) hydrazodicarboxylate

product: bis(2,2,2‐trichloroethyl) azodicarboxylate
Substituted γ‐Butyrolactones from Carboxylic Acids and Olefins: γ‐(
n
‐Octyl)‐γ‐Butyrolactone
Authors: Heiba E. I. , Dessau R. M. , Williams A. L. , Rodewald P. G.
Published: November 2003

Substituted γ‐butyrolactones from carboxylic acids and olefins: γ‐(
n
‐octyl)‐γ‐butyrolactone

product: γ‐(
n
‐octyl)‐γ‐butyrolactone
1,6‐Dimethyltricyclo[4.1.0.0
1,6
]hept‐3‐ene
Authors: Taylor R. T. , Paquette L. A.
Published: November 2003

1,6‐Dimethyltricyclo[4.1.0.0
1,6
]hept‐3‐ene

solvent: 1 L of olefin‐free petroleum ether

product: 1,6‐Dimethyltricyclo[4,1.0.02,7]hept‐3‐ene.

intermediate: 20.95 g (0.075 mol) of 7,7‐dibromo‐1,6‐dimethylbicyclo[4.1.0]hept‐3‐ene
2‐Hydroxymethyl‐2‐Cyclopentenone
Authors: Smith Amos B. , Branca Stephen J. , Guaciaro Michael A. , Wovkulich Peter M. , Korn Abner
Published: November 2003

2‐Hydroxymethyl‐2‐cyclopentenone

intermediate: 2‐Bromo‐2‐cyclopentenone.

intermediate: 2‐Bromo‐2‐cyclopentenone ethylene ketal

intermediate: 2‐hydroxymethyl‐2‐cyclopentenone ethylene ketal

product: 2‐hydroxymethyl‐2‐cyclopentenone
o
‐Isothiocyanato‐(
E
)‐Cinnamaldehyde
Authors: Farrand R. , Hull R.
Published: November 2003

o
‐isothiocyanato‐(
E
)‐cinnamaldehyde

product:
o
‐isothiocyanato‐(
E
)‐cinnamaldehyde
Methyl α‐(Bromomethyl)Acrylate
Authors: Cassady John M. , Howie Gary A. , Robinson J. Michael , Stamos Ioannis K.
Published: November 2003

Methyl α‐(bromomethyl)acrylate

reactant: 440 g (2.0 mol) of diethyl bis(hydroxymethyl)malonate

intermediate: β,β′‐dibromoisobutyric acid

intermediate: 20 g (0.077 mol) of methyl β,β′‐dibromoisobutyrate

product: Ethyl α‐(bromomethyl)acrylate

product: Methyl α‐(bromomethyl)acrylate
2‐Methyl‐3‐Phenylpropanal
Authors: Buntin S. A. , Heck R. F.
Published: November 2003

2‐Methyl‐3‐phenylpropanal

product: 2‐methyl‐3‐phenyl‐propanal, 12.05 g (82%)

byproduct: 2‐methyl‐2‐phenylpropanal
Osmium‐Catalyzed Vicinal Oxyamination of Olefins by Chloramine‐
T
:
cis
‐2‐(
p
‐Toluenesulfonamido)Cyclohexanol and 2‐Methyl‐3‐(
p
‐Toluenesulfonamido)‐2‐Pentanol
Authors: Herranz Eugenio , Sharpless K. Barry
Published: November 2003

Osmium‐catalyzed vicinal oxyamination of olefins by chloramine‐T:
cis
‐2‐(
p
‐toluenesulfonamido)cyclohexanol and 2‐methyl‐3‐(
p
‐toluenesulfonamido)‐2‐pentanol

product: cis‐2‐(p‐toluenesulfonamido)cyclohexanol

product: 2‐methyl‐3‐(p‐toluenesulfonamido)‐2‐pentanol
Osmium‐catalyzed vicinal oxyamination of olefins by
N
‐chloro‐
N
‐argentocarbamates: ethyl
threo
‐[1‐(2‐hydroxy‐1,2‐diphenylethyl)]carbamate
Authors: Herranz Eugenio , Sharpless K. Barry
Published: November 2003

Osmium‐catalyzed vicinal oxyamination of olefins by
N
‐chloro‐
N
‐argentocarbamates: ethyl
threo
‐[1‐(2‐hydroxy‐1,2‐diphenylethyl)]carbamate

product: ethyl threo‐1‐(2‐hydroxy‐1,2‐diphenylethyl)carbamate

solvent: 50 mL of petroleum ether
Preparation of Thiol Esters: S‐
tert
‐Butyl Cyclohexanecarbothioate and
S‐tert
‐Butyl 3α,7α,12α‐Trihydroxy‐5β‐cholane‐24‐thioate
Authors: Spessard Gary O. , Chan Wan Kit , Masamune S.
Published: November 2003

Preparation of thiol esters: S‐
tert
‐butyl cyclohexanecarbothioate and
S‐tert
‐butyl 3α,7α,12α‐trihydroxy‐5β‐cholane‐24‐thioate

product: S‐tert‐Butyl cyclohexanecarbothioate

reactant: 4.38 g (0.030 mol) of cyclohexanecarboxylic acid chloride

reactant: 8.82 g (0.031 mol) of the thallium(I) 2‐methylpropane‐2‐thiolate

product: S‐tert‐Butyl ester
Z
‐1‐Iodohexene
Authors: Alexakis A. , Cahiez G. , Normant J. F.
Published: November 2003

Z
‐1‐iodohexene

product: Z‐1‐iodohexene

product: EtCHCHI

product: (n‐C
5
H
11
)CHCHI

product: (n‐C
7
H
15
)CHCHI

product: EtCHCHCH
2
CH
2
CHCHI

product: HO(CH
2
)3CHCHIc

product: HO(CH
2
)8CHCHIc
Palladium‐Phosphine‐Complex‐Catalyzed Reaction of Organolithium Compounds and Alkenyl Halides: (
Z
)‐β‐[2‐(
N,N
‐Dimethylamino)Phenyl]Styrene
Authors: Murahashi Shun‐Ichi , Naota Takeshi , Tanigawa Yoshio
Published: November 2003

Palladium‐phosphine‐complex‐catalyzed reaction of organolithium compounds and alkenyl halides: (
Z
)‐β‐[2‐(
N,N
‐dimethylamino)phenyl]styrene

reactant: 30.8 g (0.100 mol) of erythro‐α,β‐dibromo‐β‐phenylpropionic acid

reactant: (
Z
)‐β‐bromostyrene

reactant: 18.2 g (0.150 mol) of
N,N
‐dimethylaniline

product: (
Z
)‐β‐[2‐(
N,N
‐dimethylamino)phenyl]styrene

reactant:
trans
‐cinnamic acid (mp 133–134°C) (Nakarai Chemicals, Japan)

product: (Z)C
6
H
5
CHCHCH
3

product: (Z)C
6
H
5
CHCHC
4
H
9

product: (Z)‐C
6
H
5
CHCHSC
6
H
5

product: (Z)‐C
6
H
5
CHCHSC
2
H
5

product: (E)‐C
6
H
5
CHCHCH
3
Selective Halogen‐Lithium Exchange Reactions of 2‐(2′‐Halophenyl)Ethyl Halides: Synthesis of 4,5‐Methylenedioxybenzocyclobutene and 1‐Phenyl‐3,4‐Dihydro‐6,7‐Methylenedioxyisoquinoline
Authors: Jakiela Dennis J. , Helquist Paul , Jones Lawrence D.
Published: November 2003

Selective halogen‐lithium exchange reactions of 2‐(2′‐halophenyl)ethyl halides: synthesis of 4,5‐methylenedioxybenzocyclobutene and 1‐phenyl‐3,4‐dihydro‐6,7‐methylenedioxyisoquinoline

reactant: 10.0 g (37.9 mmol) of 2‐(2′‐bromo‐4′,5′‐methylenedioxyphenyl)ethyl chloride

product: 4,5‐methylenedioxybenzocyclobutene

product:
1‐Phenyl‐3,4‐dihydro‐6,7‐methylenedioxyisoquinoline

intermediate: 2‐(3′,4′‐methylenedioxyphenyl)ethanol

intermediate: 2‐(2′‐bromo‐4′,5′‐methylenedioxyphenyl)ethanol
Diphenyl Phosphorazidate
Authors: Shioiri Takayuki , Yamada Shun‐ichi
Published: November 2003

Diphenyl phosphorazidate

product: diphenyl phosphorazidate
( + )‐(7
aS
)‐7a‐Methyl‐2,3,7,7a‐Tetrahydro‐1
H
‐Indene‐1,5‐(6
H
‐Dione
Authors: Hajos Zoltan G. , Parrish David R.
Published: November 2003

( + )‐(7
aS
)‐7a‐Methyl‐2,3,7,7a‐tetrahydro‐1
H
‐indene‐1,5‐(6
H
‐dione

product: ( + )‐(7aS)‐7a‐methyl‐2,3,7,7a‐tetrahydro‐1 h‐indene‐1,5‐(6H‐dione

reactant: 140 mL (120.96 g, 1.72 mol) of methyl vinyl ketone

solvent: 188 mL of N,N‐dimethyl‐formamide

intermediate: 45.5 g (0.25 mol) of the 2‐methyl‐2‐(3‐oxobutyl)‐1,3‐cyclopentanedione

intermediate: ( + )‐(3aS,7aS)‐2,3,3a,4,7,7a‐hexahydro‐3a‐hydroxy‐7a‐methyl‐1H‐indene‐1,5(6H)‐dione
(
S
)‐8a‐Methyl‐3,4,8,8a‐Tetrahydro‐1,6(2
H
, 7
H
)‐Naphthalenedione
Authors: Buchschacher Paul , Fürst A. , Gutzwiller J.
Published: November 2003

(
S
)‐8a‐Methyl‐3,4,8,8a‐Tetrahydro‐1,6(2
H
, 7
H
)‐Naphthalenedione

product: (S)‐8a‐Methyl‐3,4,8,8a‐Tetrahydro‐1,6(2H, 7H)‐Naphthalenedione

intermediate: 2‐methyl‐2‐(3‐oxobutyl)‐1,3‐cyclohexanedione

reactant: 2‐Methyl‐1,3‐cyclohexanedione

reactant: Methyl vinyl ketone, bp 34°C/120 mm
Asymmetric Reduction of α,β‐Acetylenic Ketones with
B
‐3‐Pinanyl‐9‐Borabicyclo[3.3.1]Nonane: (
R
)‐( + )‐1‐Octyn‐3‐Ol
Authors: Midland M. Mark , Graham Richard S.
Published: November 2003

Asymmetric reduction of α,β‐acetylenic ketones with
B
‐3‐pinanyl‐9‐borabicyclo[3.3.1]nonane: (
R
)‐( + )‐1‐octyn‐3‐ol

reactant: 35.3 g (0.285 mol) of 1‐octyn‐3‐one

product: 1‐octyn‐3‐ol
2‐Methyl‐2‐(Trimethylsiloxy)Pentan‐3‐one
Authors: Young Steven D. , Buse Charles T. , Heathcock Clayton H.
Published: November 2003

2‐Methyl‐2‐(trimethylsiloxy)pentan‐3‐one

intermediate: 2‐hydroxybutanenitrile

intermediate: 2‐[(1′‐ethoxy)‐1‐ethoxy]butanenitrile

intermediate: 2‐hydroxy‐2‐methylpentan‐3‐one

product: 2‐methyl‐2‐(trimethylsiloxy)pentan‐3‐one
Diastereoselective α‐Alkylation of β‐Hydroxycarboxylic Esters through Alkoxide Enolates: Diethyl (2
S
, 3
R
)‐( + )‐3‐Allyl‐2‐Hydroxysuccinate from Diethyl (
S
)‐( − )‐Malate
Authors: Seebach Dieter , Aebi Johannes , Wasmuth Daniel
Published: November 2003

Diastereoselective α‐alkylation of β‐hydroxycarboxylic esters through alkoxide enolates: diethyl (2
S
, 3
R
)‐( + )‐3‐allyl‐2‐hydroxysuccinate from diethyl (
S
)‐( − )‐malate

reactant: 9.51 g (50 mmol) of ( − )‐diethyl (
S
)‐malate

product: allylated product

product: (2
S
,3
R
)‐3‐allyl‐2‐hydroxysuccinic acid
Reduction of α‐Amino Acids: L‐Valinol
Authors: Dickman D. A. , Meyers A. I. , Smith G. A. , Gawley R. E.
Published: November 2003

Reduction of α‐amino acids: L‐valinol

product:
L
‐valinol

product: prolinol

product: alaninol

product: phenylglycinol

product: phenylalaninol

product:
N
‐benzylvalinol
2‐Alkenyl Carbinols from 2‐Halo Ketones: 2‐
E
‐Propenylcyclohexanol
Authors: Wender P. A. , Holt D. A. , Sieburth S. McN.
Published: November 2003

2‐Alkenyl carbinols from 2‐halo ketones: 2‐
E
‐propenylcyclohexanol

product: 2‐
E
‐propenylcyclohexanol
Cyclobutene
Authors: Salaün J. , Fadel A.
Published: November 2003

Cyclobutene

intermediate: Cyclobutanol

byproduct: 3‐buten‐1‐ol

intermediate: cyclobutyl tosylate

product: cyclobutene

product: 1,2‐dibromocyclobutane
Dichlorovinylation of an Enolate: 8‐Ethynyl‐8‐Methyl‐1,4‐Dioxaspiro[4.5]Dec‐6‐Ene
Authors: Kende Andrew S. , Fludzinski Pawel
Published: November 2003

Dichlorovinylation of an enolate: 8‐Ethynyl‐8‐methyl‐1,4‐dioxaspiro[4.5]dec‐6‐ene

byproduct: 6‐[(
E
)‐1,2‐dichlorovinyl]‐3‐ethoxy‐6‐methyl‐2‐cyclohexen‐1‐one

intermediate: 4‐[(
E
)‐1,2‐dichlorovinyl]‐4‐methyl‐2‐cyclohexen‐1‐one

product: 8‐[(
E
)‐1,2‐dichlorovinyl]‐8‐methyl‐1,4‐dioxaspiro[4.5]dec‐6‐ene

product: 8‐ethynyl‐8‐methyl‐1,4‐dioxaspiro[4.5]dec‐6‐ene
Electrophilic
N
‐Amination of Imide Sodium Salts with
O
‐Diphenylphosphinylhydroxylamine (DPH): 7‐Aminotheophylline
Authors: Klötzer W. , Stadlwieser J. , Raneburger J.
Published: November 2003

Electrophilic
N
‐amination of imide sodium salts with
O
‐diphenylphosphinylhydroxylamine (DPH): 7‐aminotheophylline

intermediate: O‐diphenylphosphinylhydroxylamine

solvent: 240 mL of anhydrous ethanol

reactant: 600 mL of anhydrous N‐methylpyrrolidone

reactant: 20.2 g (0.1 mol) of anhydrous theophylline sodium salt

intermediate: diphenylphosphinic acid

intermediate: 7‐benzylideneaminotheophylline

product: 7‐aminotheophylline

product: 1‐Aminoimidazole

product: 1‐Amino‐2‐nitroimi‐dazole

product: 1‐Amino‐2‐methyl‐4‐nitroimidazole

product: 1‐Aminotheobromine

product: 7‐Aminotheophylline

product: N‐Aminophthalimide
Formyl Transfer to
G
rignard Reagents with
N
‐Formylpiperidine: 3‐Phenylpropionaldehyde
Authors: Olah George A. , Arvanaghi Massoud
Published: November 2003

Formyl transfer to Grignard reagents with
N
‐formylpiperidine: 3‐phenylpropionaldehyde

product: 3‐phenylpropionaldehyde
Methyl Diformylacetate
Authors: Hutchinson C. R. , Nakane M. , Gollman H. , Knutson P. L.
Published: November 2003

Methyl Diformylacetate

intermediate: potassium monomethyl malonate

product: methyl diformylacetate
Selective Hydroboration of a 1,3,7‐Triene: Homogeraniol
Authors: Leopold Eric J.
Published: November 2003

Selective hydroboration of a 1,3,7‐triene: homogeraniol

intermediate: geranial

solvent: 200 mL of petroleum ether

intermediate: 13.0 g (86.7 mmol) of (E)‐4,8‐dimethyl‐1,3,7‐nonatriene

product: homogeraniol

intermediate: 1–2% of the Z isomer.
2,2′ : 6′,2′‐Terpyridine
Authors: Potts Kevin T. , Ralli Philip , Theodoridis George , Winslow Paul
Published: November 2003

2,2′ : 6′,2′‐Terpyridine

intermediate: 22.5 g (0.1 mol) of 3,3‐bis(methylthio)‐1‐(2‐pyridinyl)‐2‐propen‐1‐one

intermediate: 4′‐(methylthio)‐2,2′ : 6′,2″‐terpyridine

product: 2,2′ : 6′,2″‐terpyridine
Trifloroacetyl Triflate
Authors: Taylor Stephen L. , Forbus T. R. , Martin J. C.
Published: November 2003

Trifloroacetyl triflate

reactant: 85.5 g (0.75 mol) of trifluoroacetic acid (TFA)

reactant: 56.5 g (0.750 mol) of triflic acid (TfOH)

product: trifluoroacetyl triflate (TFAT), is of 99%

byproduct: trifluoroacetic anhydride (TFAA)
3‐Hydroxy‐3‐methyl‐1‐phenyl‐1‐butanone by Crossed Aldol Reaction
Authors: Mukaiyama Teruaki , Narasaka Koichi
Published: November 2003

3‐Hydroxy‐3‐methyl‐1‐phenyl‐1‐butanone by crossed aldol reaction

catalyst: Titanium tetrachloride (11.0 mL)

reactant: 19.2 g of acetophenone trimethylsilyl enol ether

product: 3‐Hydroxy‐3‐methyl‐1‐phenyl‐1‐butanone
Preparation and Three‐Carbon + Two‐Carbon Cycloaddition of Cyclopropenone 1,3‐propanediol ketal: 5,5‐Dicyano‐4‐phenyl‐2‐cyclopenten‐1‐one 1,3‐propanediol ketal
Authors: Boger Dale L. , Brotherton Christine E. , Georg Gunda I.
Published: November 2003

Preparation and three‐carbon + two‐carbon cycloaddition of cyclopropenone 1,3‐propanediol ketal: 5,5‐Dicyano‐4‐phenyl‐2‐cyclopenten‐1‐one 1,3‐propanediol ketal

intermediate: 2‐(bromomethyl)‐2‐(chloromethyl)‐1,3‐dioxane

intermediate: Cyclopropenone 1,3‐propanediol ketal

product: 5,5‐dicyano‐4‐phenyl‐2‐cyclopenten‐1‐one 1,3‐propanediol ketal
1,4‐Bis(trimethylsilyl)buta‐1,3‐diyne
Authors: Jones Graham E. , Kendrick David A. , Holmes Andrew B.
Published: November 2003

1,4‐Bis(trimethylsilyl)buta‐1,3‐diyne

solvent: petroleum ether (bp 30–40°C, 3 × 150 mL)

product: bis(trimethylsilyl)butadiyne (BTMSBD)
Geminal Acylation‐Alkylation at a Carbonyl Center Using Diethyl
N
‐Benzylideneaminomethylphosphonate: 2‐Methyl‐2‐Phenyl‐4‐Pentenal
Authors: Davidsen Steven K. , Phllips Gerald W. , Martin Stephen F.
Published: November 2003

Geminal acylation‐alkylation at a carbonyl center using diethyl
N
‐benzylideneaminomethylphosphonate: 2‐methyl‐2‐phenyl‐4‐pentenal

intermediate: N‐bromomethylphthalimide

solvent: 100‐mL portions of cold petroleum ether

intermediate: diethyl phthalimidomethylphosphonate

intermediate: diethyl aminomethylphosphonate (4)

intermediate: diethyl N‐benzylideneaminomethylphosphonate (5)

intermediate: 2‐azadiene

product: 2‐methyl‐2‐phenyl‐4‐pentenal
1,3‐Dimethyl‐3‐Methoxy‐4‐Phenylazetidinone
Authors: Hegedus Lous S. , McGuire Michael A. , Schultze Lisa M.
Published: November 2003

1,3‐Dimethyl‐3‐methoxy‐4‐phenylazetidinone

product: 1,3‐Dimethyl‐3‐methoxy‐4‐phenylazetidinone.

intermediate: 1.25 g (5.0 mmol) of [(methyl)(methoxy)carbene]pentacarbonyl chromium(0)]
tert
‐Butyl‐
tert
‐Octylamine
Authors: Corey E. J. , Gross Andrew W.
Published: November 2003

tert
‐Butyl‐
tert
‐octylamine

intermediate: 29.7 g of nitroso‐tert‐octane

intermediate: N‐tert‐butyl‐N‐tert‐octyl‐O‐tert‐butylhydroxylamine

intermediate: N‐tert‐octyl‐O‐tert‐butylhydroxylamine

product: tert‐butyl‐tert‐octylamine
Chiral 1,3‐Oxathiane from (+)‐Pulegone: Hexahydro‐4,4,7‐trimethyl‐4
H
‐1,3‐benzoxathiin
Authors: Eliel Ernest L. , Lynch Joseph E. , Kume Fumitaka , Frye Stephen V.
Published: November 2003

Chiral 1,3‐oxathiane from (+)‐pulegone: Hexahydro‐4,4,7‐trimethyl‐4
H
‐1,3‐benzoxathiin

intermediate:
cis
‐ and
trans
‐5‐Methyl‐2‐[1‐methyl‐1‐(phenylmethylthio)ethyl]cyclohexanone

reactant: 202.0 g (1.33 mol) of (+)‐pulegone

intermediate: 2‐(1‐Mercapto‐1‐methylethyl)‐5‐methylcyclohexanol

product: Hexahydro‐4,4,7‐trimethyl‐4H‐1,3‐benzoxathiin.
Diisopropyl (2
S
,3
S
)‐2,3‐
O
‐Isopropylidenetartrate
Authors: Imwinkelried René , Schiess Martin , Seebach Dieter
Published: November 2003

Diisopropyl (2
S
,3
S
)‐2,3‐
O
‐isopropylidenetartrate

product: diisopropyl (2S,3S)‐2,3‐O‐isopropylidenetartrate

byproduct: Ti(OCHMe2)4
A General Method for the Synthesis of Allenylsilanes: 1‐Methyl‐1‐(Trimethylsilyl)Allene
Authors: Danheiser Rick L. , Tsai Yeun‐Min , Fink David M.
Published: November 2003

A general method for the synthesis of allenylsilanes: 1‐methyl‐1‐(trimethylsilyl)allene

product: 1‐methyl‐1‐(trimethylsilyl)allene

byproduct: 1‐trimethylsilyl‐1‐butyne
Cyclopentanones from Carboxylic Acids via IntramolecularAcylation of Alkylsilanes: 2‐Methyl‐2‐Vinylcyclopentanone
Authors: Kuwajima Isao , Urabe Hirokazu
Published: November 2003

Cyclopentanones from carboxylic acids via intramolecular acylation of alkylsilanes: 2‐methyl‐2‐vinylcyclopentanone

intermediate: 1‐iodo‐3‐trimethylsilylpropane 1

intermediate: crude acid 3

product: 2‐methyl‐2‐vinylcyclopentanone
Reduction of carboxylic acids to aldehydes: 6‐Oxodecanal
Authors: Fujisawa Tamotsu , Sato Toshio
Published: November 2003

Reduction of carboxylic acids to aldehydes: 6‐Oxodecanal

reactant: 3.07 (0.042 mol) of N,N‐dimethylformamide

reactant: 7.45 g (0.04 mol) of 6‐oxodecanoic acid

product: 6‐oxodecanal
2‐Propyl‐1‐Azacycloheptane from Cyclohexanone Oxime
Authors: Maruoka Keiji , Nakai Shuichi , Yamamoto Hisashi
Published: November 2003

2‐Propyl‐1‐azacycloheptane from cyclohexanone oxime

intermediate: cyclohexanone oxime methanesulfonate

product: 2‐propyl‐1‐azacycloheptane
Telomerization of Isoprene with Dialkylamine:
N,N
‐Diethylnerylamine
Authors: Takabe Kunihiko , Yamada Takashi , Katagiri Takao , Tanaka Juntaro
Published: November 2003

Telomerization of isoprene with dialkylamine:
N,N
‐diethylnerylamine

product:
N,N
‐diethylnerylamine

product:
N,N
‐dimethylnerylamine

product:
N,N
‐dipropylnerylamine
Ethyl 5‐Oxo‐6‐Methyl‐6‐Heptenoate from Methacryloyl Chloride and Ethyl 4‐Iodobutyrate
Authors: Tamaru Yoshinao , Ochiai Hirofumi , Nakamura Tatsuya , Yoshida Zen‐ichi
Published: November 2003

Ethyl 5‐oxo‐6‐methyl‐6‐heptenoate from methacryloyl chloride and ethyl 4‐iodobutyrate

reactant: 13.8 g (57 mmol) of ethyl 4‐iodobutyrate

product: ethyl 5‐oxo‐6‐methyl‐6‐heptenoate
1,4‐Functionalization of 1,3‐Dienes via Palladium‐Catalyzed Chloroacetoxylation and Allylic Amination: 1‐Acetoxy‐4‐Diethylamino‐2‐Butene and 1‐Acetoxy‐4‐Benzylamino‐2‐Butene
Authors: Nyström J. E. , Rein T. , Bäckvall J. E.
Published: November 2003

1,4‐Functionalization of 1,3‐dienes via palladium‐catalyzed chloroacetoxylation and allylic amination: 1‐Acetoxy‐4‐diethylamino‐2‐butene and 1‐acetoxy‐4‐benzylamino‐2‐butene

intermediate: 1‐acetoxy‐4‐chloro‐2‐butene

product: E‐1‐acetoxy‐4‐diethylamino‐2‐butene

intermediate: 1‐Acetoxy‐4‐benzylamino‐2‐butene
Palladium(0)‐Catalyzed
syn
‐1,4‐Addition of Carboxylic Acids to Cyclopentadiene Monoepoxide:
cis
‐3‐Acetoxy‐5‐Hydroxycyclopent‐1‐Ene
Authors: Deardorff Donald R. , Myles David C.
Published: November 2003

Palladium(0)‐catalyzed
syn
‐1,4‐addition of carboxylic acids to cyclopentadiene monoepoxide:
cis
‐3‐acetoxy‐5‐hydroxycyclopent‐1‐ene

product:
cis
‐3‐acetoxy‐5‐hydroxycyclopent‐1‐ene

product: 4‐Acetoxy‐2‐cyclopentenone