bluuebunny/crossref_metadata_2025_split huggingface dataset:
α‐Chlorination of Carboxylic Acids Mediated by Chlorosulfonic Acid: ε‐Benzoylamino‐α‐chlorocaproic Acid
Authors: Ogata Yoshiro , Sugimoto Toshiyuki , Inaishi Morio 
Published: November 2003

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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)
Cyclobutanone
Authors: Krumpolc Miroslav , Rocek Jan 
Published: November 2003

Abstract

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

Abstract

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

Abstract

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

AbstractDiels‐Alder reaction of 1,2,4,5‐hexatetraene: Tetramethyl[2.2]paracyclophane‐4,5,12,13‐tetracarboxylateintermediate: 1,2,4,5‐hexatetraenereactant: 69.4 g (60 mL, 0.49 mol) of dimethyl acetylenedicarboxylateproduct: tetramethyl[2.2]paracyclophane‐4,5,12,13‐tetracarboxylate
N
‐(2,4‐Diformyl‐5‐Hydroxyphenyl)Acetamide
Authors: Hocker Jürgen , Giesecke Henning 
Published: November 2003

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

AbstractMethyl α‐(bromomethyl)acrylatereactant: 440 g (2.0 mol) of diethyl bis(hydroxymethyl)malonateintermediate: β,β′‐dibromoisobutyric acidintermediate: 20 g (0.077 mol) of methyl β,β′‐dibromoisobutyrateproduct: Ethyl α‐(bromomethyl)acrylateproduct: Methyl α‐(bromomethyl)acrylate
2‐Methyl‐3‐Phenylpropanal
Authors: Buntin S. A. , Heck R. F. 
Published: November 2003

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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
( + )‐(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

Abstract

( + )‐(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

Abstract

(
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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

product: 2‐
E
‐propenylcyclohexanol
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

Abstract

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

Abstract

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

Abstract

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

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

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

byproduct: 1‐trimethylsilyl‐1‐butyne