bluuebunny/crossref_metadata_2025_split huggingface dataset:
p
‐Chlorophenoxymethyl Chloride
Authors: Gross H. , Bürger W. 
Published: November 2003

Abstract

p
‐Chlorophenoxymethyl chloride

byproduct: phosphorus trichloride

product:
p
‐chlorophenoxymethyl chloride

product: 2,4‐dichlorophenoxymethyl chloride
Diphenyl‐
p
‐Bromophenylphosphine
Authors: Schiemenz G. P. 
Published: November 2003

Abstract

Diphenyl‐
p
‐bromophenylphosphine

reactant: 15 ml. of a solution of 88.5 g. (0.38 mole) of
p
‐dibromobenzene

product: diphenyl‐
m
‐bromophenyl‐

product: diphenyl‐
p
‐chlorophenylphosphine

product: diphenyl‐
p
‐bromophenylphosphine
Methyl Ketones from Carboxylic Acids: Cyclohexyl Methyl Ketone
Authors: Bare Thomas M. , House Herbert O. 
Published: November 2003

Abstract

Methyl ketones from carboxylic acids: cyclohexyl methyl ketone

solvent: Commercial 1,2‐dimethoxyethane, b.p. 85–86°, purchased from Eastman Organic Chemicals, was distilled from lithium aluminum hydride before use

reactant: cyclohexanecarboxylic acid, m.p. 31–32°, purchased from Aldrich Chemical Company was used without further purification

product: cyclohexyl methyl ketone
exo/endo
‐7‐Norcaranol
Authors: Schöllkopf U. , Paust J. , Patsch M. R. 
Published: November 2003

Abstract

exo/endo
‐7‐norcaranol

reactant: 49.0 g. (0.300 mole) of dichloromethyl 2‐chloroethyl ether

intermediate:
exo/endo
‐7‐(2‐chloroethoxy)bicyclo[4.1.0]heptane

product:
exo/endo
‐7‐norcaranol

reactant: 2‐Ethoxy‐1,3‐dioxolane

intermediate: 2‐chloroethyl formate

byproduct: Isopropyl 2‐chloroethyl ether

product:
exo
‐7‐norcaranol
2,4,6‐Triphenylnitrobenzene
Authors: Dimroth K. , Berndt A. , Reichardt C. 
Published: November 2003

Abstract2,4,6‐Triphenylnitrobenzenereactant: 21 ml. (24 g., 0.39 mole) of nitromethanesolvent: Triethylamine (70 ml., 51 g.)product: 2,4,6‐triphenylnitrobenzene
cis
‐4‐
tert
‐Butylcyclohexanol
Authors: Eliel E. L. , Doyle T. W. , Hutchins R. O. , Gilbert E. C. 
Published: November 2003

Abstract

cis
‐4‐
tert
‐Butylcyclohexanol

product:
cis
‐4‐
tert
‐butylcyclohexanol
trans,trans
‐1,3‐Butadiene‐1,4‐diyl Diacetate
Authors: Carlson Robert M. , Hill Richard K. 
Published: November 2003

Abstract

trans,trans
‐1,3‐Butadiene‐1,4‐diyl diacetate

intermediate:
trans
‐7,8‐diacetoxybicyclo[4.2.0]octa‐2,4‐diene

solvent: petroleum ether

product:
trans,trans
‐1,3‐butadiene‐1,4‐diyl diacetate
Diethyl
tert
‐Butylmalonate
Authors: Eliel E. L. , Hutchins R. O. , Knoeber M. 
Published: November 2003

Abstract

Diethyl
tert
‐butylmalonate

reactant: 400 g. (2.50 moles) of diethyl malonate

intermediate: diethyl isopropylidenemalonate

product: diethyl
tert
‐butylmalonate
2,2‐Dimethyl‐4‐Phenylbutyric Acid
Authors: Creger P. L. 
Published: November 2003

Abstract2,2‐Dimethyl‐4‐phenylbutyric acidreactant: 7.75 g. (0.0767 mole) of diisopropylamineproduct: 2,2‐dimethyl‐4‐phenylbutyric acid
2,3‐Diphenyl‐1,3‐butadiene
Authors: Iwai Issei , Ide Junya 
Published: November 2003

Abstract

2,3‐Diphenyl‐1,3‐butadiene

reactant: 30 ml. of anhydrous dimethyl sulfoxide

product: 2,3‐diphenyl‐1,3‐butadiene
Directed Aldol Condensations: β‐Phenylcinnamaldehyde
Authors: Wittig G. , Hesse A. 
Published: November 2003

Abstract

Directed aldol condensations: β‐phenylcinnamaldehyde

reactant: 99.2 g. (1.00 mole) of freshly distilled cyclohexylamine

reactant: 44.1 g. (1.00 mole) of freshly distilled acetaldehyde

intermediate:
N
‐ethylidenecyclohexylamine

solvent: 2.53 g. (3.60 ml. or 0.0250 mole) of pure diisopropylamine

intermediate:
N
‐(3‐hydroxy‐3,3‐diphenylpropylidene)cyclohexylamine

product: β‐phenylcinnamaldehyde
Bicyclo[3.2.1]octan‐3‐one
Authors: Jefford C. W. , Gunsher J. , Hill D. T. , Brun P. , Le Gras J. , Waegell B. 
Published: November 2003

Abstract

Bicyclo[3.2.1]octan‐3‐one

solvent: 400 ml. of petroleum ether

intermediate:
exo
‐3,4‐dichlorobicyclo[3.2.1]oct‐2‐ene

intermediate: 3‐chlorobicyclo[3.2.1]oct‐2‐ene

product: bicyclo[3.2.1]octan‐3‐one
Dehydroxylation of Phenols; Hydrogenolysis of Phenolic Ethers: Biphenyl
Authors: Musliner Walter J. , Gates John W. 
Published: November 2003

Abstract

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

Abstract

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

product: 1‐bromo‐3‐chlorocyclobutane
2‐Acetyl‐1,3‐Cyclopentanedione
Authors: Merényi Ferenc , Nilsson Martin 
Published: November 2003

Abstract

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

Abstract

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
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

Abstract

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

Abstract

(−)‐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

Abstract

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
3‐Acetyl‐2,4‐Dimethylfuran
Authors: Howes P. D. , Stirling C. J. M. 
Published: November 2003

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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
1‐Bromo‐3‐methyl‐2‐butanone
Authors: Gaudry M. , Marquet A. 
Published: November 2003

Abstract

1‐Bromo‐3‐methyl‐2‐butanone

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

byproduct: 3‐bromo‐3‐methyl‐2‐butanone
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

Abstract

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

Abstract

6,7‐Dimethoxy‐3‐isochromanone

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

product: 6,7‐dimethoxy‐3‐isochromanone
Phase‐Transfer
H
ofmann Carbylamine Reaction:
tert
‐Butyl Isocyanide
Authors: Gokel George W. , Widera Ronald P. , Weber William P. 
Published: November 2003

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract2,3‐Dicyanobutadiene as a reactive intermediate byin situgeneration from 1,2‐dicyanocyclobutene: 2,3‐dicyano‐1,4,4a,9a‐tetrahydrofluoreneintermediate: 1‐Chloro‐1,2‐dicyanocyclobutane(1)intermediate: 1,2‐Dicyanocyclobutene(2)reactant: 131 g. (1.30 moles) of triethylamineproduct: 2,3‐Dicyano‐1,4,4a,9a‐tetrahydrofluorene(3)reactant: 23.3 g. (0.201 mole) of indeneproduct: 2,3‐dicyanofluoreneproduct: 4,5‐Dicyanotricyclo‐[6.2.1.02,7]undeca‐4,9‐dieneproduct: 8,9‐Dicyano‐6b,7,10,10a‐tetrahydrofluorantheneproduct: 3,4‐Dicyanobicyclo[4.3.0]non‐3‐eneproduct: 1,2‐Dicyanocyclohexeneproduct: 1,2‐Dicyano‐4,5‐diphenylcyclohexeneproduct: 1,2‐Dicyano‐4‐butoxycyclohexeneproduct: 1,2‐Dicyano‐4,5‐trans‐dichlorocyclohexeneproduct: 1,2‐Dicyano‐4‐(2 ‐pyridyl)cyclohexene
Fluorinations with Pyridinium Polyhydrogen Fluoride Reagent: 1‐Fluoroadamantane
Authors: Olah George A. , Watkins Michael 
Published: November 2003

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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