bluuebunny/crossref_metadata_2025_split huggingface dataset:
tert
‐Butylcyanoketene
Authors: Weyler Walter , Duncan Warren G. , Liewen Margo Beth , Moore Harold W. 
Published: November 2003

Abstract

tert
‐Butylcyanoketene

reactant: 110 g. (0.500 mole) of 2,5‐di‐
tert
‐butyl‐1,4‐benzoquinone

intermediate: 2,5‐di‐
tert
‐butyl‐5,6‐dichloro‐2‐cyclohexene‐1,4‐dione

intermediate: 3‐chloro‐2,5‐di‐
tert
‐butyl‐1,4‐benzoquinone

intermediate: 2,5‐di‐
tert
‐butyl‐3,5,6‐trichloro‐2‐cyclohexene‐1,4‐dione

intermediate: 2,5‐di‐
tert
‐butyl‐3,6‐dichloro‐1,4‐benzoquinone

intermediate: 3,6‐diazido‐2,5‐di‐
tert
‐butyl‐1,4‐benzoquinone

product:
tert
‐butylcyanoketene
(
E
)‐4‐Hexen‐1‐ol
Authors: Paul Raymond , Riobé Olivier , Maumy Michel 
Published: November 2003

Abstract

(
E
)‐4‐hexen‐1‐ol

reactant: 118 g. (1.40 moles) of dihydropyran

reactant: Methyl bromide (200 g., 2.15 moles)

intermediate:
cis
‐ and
trans
‐3‐chloro‐2‐methyltetrahydropyran

product: (
E
)‐4‐hexen‐1‐ol
17β‐Hydroxy‐5‐Oxo‐3,5‐
seco
‐4‐Norandrostane‐3‐Carboxylic Acid
Authors: Milewich L. , Axelrod L. R. 
Published: November 2003

Abstract

17β‐Hydroxy‐5‐oxo‐3,5‐
seco
‐4‐norandrostane‐3‐carboxylic acid

product: 17β‐hydroxy‐5‐oxo‐3,5‐
seco
‐4‐norandrostane‐3‐carboxylic acid
1,6‐Oxido[10]Annulene
Authors: Vogel E. , Klug W. , Breuer A. 
Published: November 2003

Abstract

1,6‐Oxido[10]Annulene

solvent: 50 ml. of petroleum ether

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

intermediate: 117 g. (0.250 mole) of finely powdered 3,4,8,9‐tetrabromo‐11‐oxatricyclo[4.4.1.0
1,6
]undecane

product: 1,6‐oxido[10]annulene
Preparation of
N
‐Aminoaziridines:
trans
‐1‐Amino‐2,3‐Diphenylaziridine, 1‐Amino‐2‐Phenylaziridine, and 1‐Amino‐2‐Phenylaziridinium Acetate
Authors: Müller Robert K. , Joos Renato , Felix Dorothee , Schreiber Jakob , Wintner Claude , Eschenmoser A. 
Published: November 2003

Abstract

Preparation of
N
‐aminoaziridines:
trans
‐1‐amino‐2,3‐diphenylaziridine, 1‐amino‐2‐phenylaziridine, and 1‐amino‐2‐phenylaziridinium acetate

intermediate: trans‐2,3‐
Diphenyl
‐1‐
phthalimidoaziridine

product: trans‐1‐
Amino
‐2,3‐
diphenylaziridine

product:
Styrene glycol dimesylate

product: 1‐amino‐2‐phenylaziridine

product: 1‐amino‐2‐phenylaziridinium acetate
Esterification of Carboxylic Acids with Trialkyloxonium Salts: Ethyl and Methyl 4‐Acetoxybenzoates
Authors: Raber Douglas J. , Gariano Patrick , Brod Albert O. , Gariano Anne L. , Guida Wayne C. 
Published: November 2003

Abstract

Esterification of carboxylic acids with trialkyloxonium salts: ethyl and methyl 4‐acetoxybenzoates

reactant: 1.80 g. (0.0100 mole) of 4‐acetoxybenzoic acid

product: ethyl 4‐acetoxybenzoate

product: methyl 4‐acetoxybenzoate
Polymeric Carbodiimide. Preparation
Authors: Weinshenker Ned M. , Shen Chah M. , Wong Jack Y. 
Published: November 2003

Abstract

Polymeric carbodiimide. preparation

reactant: 10.0 g. of chloromethylated polystyrene beads

intermediate: phthalimido polymer

intermediate: benzylamine

intermediate: 2‐propyl urea polymer

product: polymeric carbodiimide
Cyclobutanone from Methylenecyclopropane
via
Oxaspiropentane
Authors: Salaun J. R. , Champion J. , Conia J. M. 
Published: November 2003

Abstract

Cyclobutanone from methylenecyclopropane
via
oxaspiropentane

reactant: 228 g. (2.52 moles) of 3‐chloro‐2‐methyl‐1‐propene

intermediate: methylenecyclopropane

intermediate: oxaspiropentane (35%)

product: cyclobutanone
Di‐
tert
‐Butyl Dicarbonate
Authors: Pope Barry M. , Yamamoto Yutaka , Tarbell D. Stanley 
Published: November 2003

Abstract

Di‐
tert
‐butyl dicarbonate

solvent: 550 ml. of anhydrous tetrahydrofuran

intermediate: di‐
tert
‐butyl tricarbonate

product: di‐
tert
‐butyl dicarbonate
3‐Phenyl‐2
H
‐Azirine‐2‐Carboxaldehyde
Authors: Padwa Albert , Blacklock Thomas , Tremper Alan 
Published: November 2003

Abstract

3‐Phenyl‐2
H
‐azirine‐2‐carboxaldehyde

intermediate: (1‐
Azido
‐2‐
iodo
‐3,3‐
dimethoxypropyl)benzene

intermediate: (1‐
Azido
‐3,3‐
dimethoxy
‐1‐
propenyl)benzene

intermediate: 2‐(
Dimethoxymethyl)
‐3‐
phenyl
‐2H‐
azirine

product: 3‐
Phenyl
‐2H‐
azirine
‐2‐
carboxaldehyde

reactant: Cinnamaldehyde dimethyl acetal
Boranes in Functionalization of Dienes to Cyclic Ketones: Bicyclo[3.3.1]nonan‐9‐one
Authors: Carlson Bruce A. , Brown Herbert C. 
Published: November 2003

Abstract

Boranes in functionalization of dienes to cyclic ketones: bicyclo[3.3.1]nonan‐9‐one

product: bicyclo[3.3.1]nonan‐9‐one
Boranes in Functionalization of Olefins to Amines: 3‐Pinanamine
Authors: Rathke Michael W. , Millard Alan A. 
Published: November 2003

Abstract

Boranes in functionalization of olefins to amines: 3‐pinanamine

product: 3‐
Pinanamine
(3)

reactant: 27.25 g. (0.2004 mole) of (±)‐α‐pinene

reactant: 15.6 g. (0.110 mole) of boron trifluoride diethyl etherate

intermediate: Di‐3‐pinanylborane (2)

intermediate: Hydroxylamine‐
O
‐sulfonic acid (1) (24.9 g., 0.220 mole) in 100 ml. of diglyme
Carbene Generation by α‐Elimination with Lithium 2,2,6,6‐Tetramethylpiperidide: 1‐Ethoxy‐2‐
p
‐Tolylcyclopropane
Authors: Dougherty Charles M. , Olofson Roy A. 
Published: November 2003

Abstract

Carbene generation by α‐elimination with lithium 2,2,6,6‐tetramethylpiperidide: 1‐ethoxy‐2‐
p
‐tolylcyclopropane

reactant: 7.06 g. (0.0501 mole) of 2,2,6,6‐tetramethylpiperidine

product: 1‐ethoxy‐2‐
p
‐tolylcyclopropane

product: 1‐methoxy‐2‐phenylcyclopropane
Cyclopentenones from α,α′‐Dibromoketones and Enamines: 2,5‐Dimethyl‐3‐Phenyl‐2‐Cyclopenten‐1‐One
Authors: Noyori R. , Yokoyama K. , Hayakawa Y. 
Published: November 2003

Abstract

Cyclopentenones from α,α′‐dibromoketones and enamines: 2,5‐dimethyl‐3‐phenyl‐2‐cyclopenten‐1‐one

reactant: 2,4‐dibromo‐3‐pentanone (1)

reactant: 75.0 g. (0.625 mole) of acetophenone

reactant: α‐morpholinostyrene

product: 2,5‐
Dimethyl
‐3‐
phenyl
‐2‐
cyclopenten
‐1‐
one
(3)
Nitrones for Intramolecular 1,3‐Dipolar Cycloadditions: Hexahydro‐1,3,3,6‐Tetramethyl‐2,1‐Benzisoxazoline
Authors: LeBel Norman A. , Hwang Dorothy 
Published: November 2003

Abstract

Nitrones for intramolecular 1,3‐dipolar cycloadditions: hexahydro‐1,3,3,6‐tetramethyl‐2,1‐benzisoxazoline

reactant: 25.0 g. (0.16 mole) of 3,7‐dimethyl‐6‐octenal

reactant: 23.4 g. (0.280 mole) of
N
‐methylhydroxylamine hydrochloride

product: hexahydro‐1,3,3,6‐tetramethyl‐2,1‐benzisoxazoline
3‐Trimethylsilyl‐3‐Buten‐2‐one: A
M
ichael acceptor
Authors: Boeckman Robert K. , Blum David M. , Ganem Bruce , Halvey Neil 
Published: November 2003

Abstract

3‐Trimethylsilyl‐3‐buten‐2‐one: A Michael acceptor

intermediate:
Vinyltrimethylsilane

intermediate: (1‐Bromoethynl)trimethylsilane

intermediate: 3‐
Trimethylsilyl
‐3‐
buten
‐2‐
ol

product: 3‐
Trimethylsilyl
‐3‐
buten
‐2‐
one
Alkynes
via
Phase Transfer–Catalyzed Dehydrohalogenation: Propiolaldehyde Diethyl Acetal
Authors: Le Coq A. , Gorgues A. 
Published: November 2003

Abstract

Alkynes
via
phase transfer–catalyzed dehydrohalogenation: propiolaldehyde diethyl acetal

intermediate: 2,3‐dibromopropionaldehyde diethyl acetal

reactant: 100 g. (0.295 mole) of tetrabutylammonium hydrogen sulfate

product: propiolaldehyde diethyl acetal

reactant: tetrabutylammonium bromide

product: diphenylacetylene

product: phenylacetylene

product:
p
‐tolylacetylene

product: 3‐chloropropiolaldehyde diethyl acetal
Diazo Transfer by Means of Phase‐Transfer Catalysis: Di‐
tert
‐butyl Diazomalonate
Authors: Ledon Henry J. 
Published: November 2003

Abstract

Diazo transfer by means of phase‐transfer catalysis: Di‐
tert
‐butyl diazomalonate

product: di‐
tert
‐butyl diazomalonate
Diels‐Alder Addition of Perchlorobenzyne: Benzobarrelene
Authors: Hales Neil J. , Heaney Harry , Hollinshead John H. , Singh Pritpal 
Published: November 2003

Abstract

Diels‐Alder addition of perchlorobenzyne: benzobarrelene

intermediate:
Tetrachlorobenzobarrelene

product:
Benzobarrelene

reactant: Technical‐grade hexachlorobenzene was purchased by the submitters from BDH Chemicals, Ltd.

solvent: Low‐boiling petroleum ether (b.p. 30–50° or 40–60°)

product: R
1
= OMe; R
2
= R
3
= R
4
= R
5
= H

product: R
1
= OMe; R
2
= R
5
= Me; R
3
= R
4
= H

product: R
1
= OMe; R
2
= R
4
= Me; R
3
= R
5
= H

product: R
1
= OMe; R
2
= Me; R
3
= R
4
= R
5
= H
StereoselectiveHydroxylation with Thallium(I) Acetate and Iodine:
trans
‐ and
cis
‐1,2‐Cyclohexanediols
Authors: Cambie R. C. , Rutledge P. S. 
Published: November 2003

Abstract

Stereoselective hydroxylation with thallium(I) acetate and iodine:
trans
‐ and
cis
‐1,2‐cyclohexanediols

solvent: 40 ml. of dried acetic acid

intermediate:
trans
‐1,2‐cyclohexanediol diacetate

product:
trans
‐1,2‐cyclohexanediol

product:
cis
‐1,2‐cyclohexanediol
Conversion of Ketones to Cyanohydrins: Benzophenone Cycanohydrin
Authors: Gassman Paul G. , Talley John J. 
Published: November 2003

Abstract

Conversion of Ketones to Cyanohydrins: Benzophenone Cycanohydrin

intermediate: O‐(trimethylsilyl) benzophenone cyanohydrin

product: Benzophenone cyanohydrin

product: Cyclohexanone cyanohydrin

product: Cyclooctanone cyanohydrin

product: Fluorenone cyanohydrin

product: tert‐Butyl phenyl ketone cyanohydrin

product: p‐Chloroacetophenone cyanohydrin

product: p‐Nitroacetophenone cyanohydrin

product: p‐Acetylbenzonitrile cyanohydrin

product: p‐Methoxyacetophenone cyanohydrin

product: p‐Methylacetophenone cyanohydrin
Methyl 4‐Hydroxy‐2‐Butynoate
Authors: Earl R. A. , Townsend L. B. 
Published: November 2003

Abstract

Methyl 4‐hydroxy‐2‐butynoate

intermediate:
Tetrahydropyranyl derivative of propargyl alcohol
[
tetrahydro
‐2‐(2‐
propynyloxy
)‐2H‐
pyran
]

product: methyl 4‐hydroxy‐2‐butynoate

reactant: 4‐hydroxy‐2‐butynoic acid
2‐Nitropropene
Authors: Miyashita Masaaki , Yanami Tetsuji , Yoshikoshi Akira 
Published: November 2003

Abstract

2‐Nitropropene

reactant: 52.5 g (0.50 mol) of 2‐nitro‐1‐propanol

product: 2‐nitropropene

product: 1‐nitro‐1‐propene

product: 2‐nitro‐1‐butene

product: 2‐nitro‐2‐butene
Preparation of 4‐Alkyl‐and 4‐Halobenzoyl Chlorides: 4‐Pentylbenzoyl Chloride
Authors: Neubert Mary E. , Fishel D. L. 
Published: November 2003

AbstractPreparation of 4‐alkyl‐and 4‐halobenzoyl chlorides: 4‐pentylbenzoyl chlorideproduct: 4‐pentylbenzoyl chloridebyproduct: 4,4′‐disubstituted benzophenone
Enantioselective Addition of Butyllithium in the Presence of the Chiral Cosolvent
DDB
: (
R
)‐( + )‐1‐Phenyl‐1‐Pentanol
Authors: Seebach Dieter , Hidber August 
Published: November 2003

Abstract

Enantioselective addition of butyllithium in the presence of the chiral cosolvent DDB: (
R
)‐( + )‐1‐phenyl‐1‐pentanol

solvent: 400 mL of 2‐methylbutane (isopentane)

solvent: 24.6 g (27.5 mL, 0.12 mol) of (
S,S
)‐( + )‐
N,N,N′,N′
‐tetramethyl‐1,4‐diamino‐2,3‐dimethoxybutane (DDB)

product: 1‐phenyl‐1‐pentanol

solvent: petroleum ether
Ethyl α‐(Bromomethyl)acrylate
Authors: Ramarajan K. , Ramalingam K. , O'Donnell D. J. , Berlin K. D. 
Published: November 2003

Abstract

Ethyl α‐(bromomethyl)acrylate

reactant: 55.0 g (0.25 mol) of diethyl bis(hydroxymethyl)malonate

intermediate: α‐(bromomethyl)acrylic acid

solvent: Skelly‐solve‐B

product: ethyl α‐(bromomethyl)acrylate
Spiro[5.7]trideca‐1,4‐dien‐3‐one
Authors: Kane Vinayak V. , Jones Maitland 
Published: November 2003

Abstract

Spiro[5.7]trideca‐1,4‐dien‐3‐one

intermediate: 1‐(cyclooctylidenemethyl)piperidine

reactant: methyl vinyl ketone (6.44 g, 0.092 mol)

intermediate: spiro[5.7]tridec‐1‐en‐3‐one

product: spiro[5.7]trideca‐1,4‐dien‐3‐one
Preparation and
D
iels–
A
lder Reaction of a Highly Nucleophilic Diene:
trans
‐1‐Methoxy‐3‐Trimethylsiloxy‐1,3‐Butadiene and 5β‐Methoxycyclohexan‐1‐One‐3β,4β‐Dicarboxylic Acid Anhydride
Authors: Danishefsky Samuel , Kitahara Takeshi , Schuda Paul F. 
Published: November 2003

Abstract

Preparation and Diels–Alder reaction of a highly nucleophilic diene:
trans
‐1‐methoxy‐3‐trimethylsiloxy‐1,3‐butadiene and 5β‐methoxycyclohexan‐1‐one‐3β,4β‐dicarboxylic acid anhydride

product:
trans
‐1‐methoxy‐3‐trimethylsiloxy‐1,3‐butadiene

product:
5β‐Methoxycyclohexan‐1‐one‐3β,4β‐dicarboxylic acid anhydride

byproduct: triethylamine hydrochloride
The
C
‐Arylation of β‐Dicarbonyl Compounds: Ethyl 1‐(
p
‐Methoxyphenyl)‐2‐Oxocyclohexanecarboxylate
Authors: Kozyrod Robert P. , Pinhey John T. 
Published: November 2003

Abstract

The
C
‐arylation of β‐dicarbonyl compounds: Ethyl 1‐(
p
‐methoxyphenyl)‐2‐oxocyclohexanecarboxylate

solvent: 1.5 L of hexane

intermediate:
p
‐methoxyphenyllead triacetate

product: ethyl 1‐(
p
‐methoxyphenyl)‐2‐oxocyclohexanecarboxylate
α‐
tert
‐Alkylation of Ketones: 2‐
tert
‐Pentylcyclopentanone
Authors: Reetz M. T. , Chatziiosifidis I. , Hübner F. , Heimbach H. 
Published: November 2003

Abstract

α‐
tert
‐alkylation of ketones: 2‐
tert
‐pentylcyclopentanone

intermediate: 1‐trimethylsiloxycyclopentene

reactant: 11.7 g (0.11 mol) of 2‐chloro‐2‐methylbutane

product: 2‐
tert
‐pentylcyclopentanone
3‐(1‐Hydroxybutyl)‐1‐methylpyrrole and 3‐Butyroyl‐1‐methylpyrrole
Authors: Gilow H. M. , Jones G. 
Published: November 2003

Abstract

3‐(1‐Hydroxybutyl)‐1‐methylpyrrole and 3‐butyroyl‐1‐methylpyrrole

product: 3‐(1‐Hydroxybutyl)‐1‐methylpyrrole (1)

reactant: 60 mL (55 g, 0.676 mol) of 1‐methylpyrrole

reactant: 65 mL (54 g, 0.936 mol) of butyraldehyde

product: 3‐Butyroyl‐1‐methylpyrrole (2)

product: 3‐acetyl‐1‐methylpyrrole
Photocyclization of an Enone to an Alkene: 6‐Methylbicyclo[4.2.0]Octan‐2‐One
Authors: Cargill R. L. , Dalton J. R. , Morton G. H. , Caldwell W. E. 
Published: November 2003

Abstract

Photocyclization of an enone to an alkene: 6‐methylbicyclo[4.2.0]octan‐2‐one

product: 6‐methylbicyclo[4.2.0]octan‐2‐one
Copper(
I
)‐Catalyzed Photocycloaddition: 3,3‐Dimethyl‐
cis
‐bicyclo[3.2.0]heptan‐2‐one
Authors: Salomon Robert G. , Ghosh Subrata 
Published: November 2003

Abstract

Copper(I)‐catalyzed photocycloaddition: 3,3‐Dimethyl‐
cis
‐bicyclo[3.2.0]heptan‐2‐one

intermediate: 2,2‐dimethyl‐4‐pentenal

intermediate: 4,4‐dimethyl‐1,6‐heptadien‐3‐ol

intermediate: 3,3‐dimethyl‐
cis
‐bicyclo[3.2.0]heptan‐2‐ol

product: 3,3‐dimethyl‐
cis
‐bicyclo[3.2.0]heptan‐2‐one

intermediate: 3,3‐dimethyl‐
endo
‐
cis
‐bicyclo[3.2.0]heptan‐2‐ol

intermediate: 3,3‐dimethyl‐
exo
‐
cis
‐bicyclo[3.2.0]heptan‐2‐ol
Thiete 1,1‐dioxide and 3‐Chlorothiete 1,1‐dioxide
Authors: Sedergran Thomas C. , Dittmer Donald C. 
Published: November 2003

Abstract

Thiete 1,1‐dioxide and 3‐chlorothiete 1,1‐dioxide

intermediate: Thietane 1,1‐dioxide (14.0 g, 0.132 mol)

intermediate: 3‐chlorothietane 1,1‐dioxide (8.0 g, 0.057 mol)

intermediate: 3,3‐dichlorothietane 1,1‐dioxide (4.0 g, 0.023 mol)

product: thiete 1,1‐dioxide

product: 3‐Chlorothiete 1,1‐dioxide
Yeast Reduction of Ethyl Acetoacetate: (
S
)‐( + )‐Ethyl 3‐Hydroxybutanoate
Authors: Seebach Dieter , Sutter Marius A. , Weber Roland H. , Züger Max F. 
Published: November 2003

Abstract

Yeast reduction of ethyl acetoacetate: (
S
)‐( + )‐ethyl 3‐hydroxybutanoate

reactant: 20.0 g (0.154 mol) of ethyl acetoacetate

product: (S)‐( + )‐ethyl 3‐hydroxybutanoate

reactant: ethyl (S)‐( + )‐3‐(3′,5′‐dinitrobenzoyloxy)butanoate

product: methyl 3‐hydroxybutanoate

byproduct: (R‐)‐( − )‐Ethyl 3‐hydroxybutanoate
Asymmetric Hydroboration of 5‐Substituted Cyclopentadienes: Synthesis of Methyl (1
R
,5
R
)‐5‐Hydroxy‐2‐Cyclopentene‐1‐Acetate
Authors: Partridge John J. , Chadha Naresh K. , Uskokovic Milan R. 
Published: November 2003

Abstract

Asymmetric hydroboration of 5‐substituted cyclopentadienes: synthesis of methyl (1
R
,5
R
)‐5‐hydroxy‐2‐cyclopentene‐1‐acetate

intermediate: Cyclopentadiene

reactant: (−)‐α‐pinene

product: methyl (1R,5R)‐5‐hydroxy‐2‐cyclopentene‐1‐acetate

reactant: ( + )‐α‐pinene

product: methyl (1S,5S)‐5‐hydroxy‐2‐cyclopentene‐1‐acetate

unknown: R = CH
3

unknown: R = CH
2
CO
2
CH
3

unknown: R = CH
2
CO
2
‐t‐Bu
(2
SR
,3
SR
)‐2,4‐Dimethyl‐3‐hydroxypentanoic Acid
Authors: Montgomery Stephen H. , Pirrung Michael C. , Heathcock Clayton H. 
Published: November 2003

Abstract

(2
SR
,3
SR
)‐2,4‐Dimethyl‐3‐hydroxypentanoic acid

intermediate: 2,6‐dimethylphenyl propanoate

intermediate: 2′,6′‐Dimethylphenyl (2
SR
,3
SR
)‐2,4‐dimethyl‐3‐hydroxypentanoate.

product: (2
SR
,3
SR
)‐2,4‐dimethyl‐3‐hydroxypentanoic acid
Ricinelaidic Acid Lactone
Authors: Thalmann Adolf , Oertle Konrad , Gerlach Hans 
Published: November 2003

Abstract

Ricinelaidic acid lactone

intermediate: ricinelaidic acid

reactant: 308 mg (1.4 mmol) of 2,2′‐dipyridyl disulfide

product: ricinelaidic acid lactone
Methyl Phenylacetylacetate from Phenylacetyl Chloride and Meldrum's Acid
Authors: Oikawa Y. , Yoshioka T. , Sugano K. , Yonemitsu Osamu 
Published: November 2003

Abstract

Methyl phenylacetylacetate from phenylacetyl chloride and Meldrum's acid

reactant: 25.0 g (0.16 mol) of freshly distilled phenylacetyl chloride

intermediate: acyl Meldrum's acid

product: methyl phenylacetylacetate
One‐Step Homologation of Acetylenes to Allenes: 4‐Hydroxynona‐1,2‐diene
Authors: Crabbé Pierre , Nassim Bahman , Robert‐Lopes Maria‐Teresa 
Published: November 2003

Abstract

One‐Step Homologation of Acetylenes to Allenes: 4‐Hydroxynona‐1,2‐diene

product: 4‐hydroxynona‐1,2‐diene
Deoxygenation of Secondary Alcohols: 3‐Deoxy‐1,2:5,6‐Di‐
O
‐Isopropylidene‐α‐
D
‐
ribo
‐Hexofuranose
Authors: Iacono S. , Rasmussen James R. 
Published: November 2003

Abstract

Deoxygenation of secondary alcohols: 3‐deoxy‐1,2:5,6‐di‐
O
‐isopropylidene‐α‐D‐
ribo
‐hexofuranose

intermediate: 19.25 g (0.055 mol) of 1,2:5,6‐di‐
O
‐isopropylidene‐3‐
O
‐(
S
‐methyldithiocarbonate)‐α‐
D
‐glucofuranose

product: 3‐Deoxy‐1,2:5,6‐di‐
O
‐isopropylidene‐α‐
D
‐
ribo
‐hexofuranose
Diethyl [(2‐Tetrahydropyranyloxy)Methyl]Phosphonate
Authors: Kluge Arthur F. 
Published: November 2003

Abstract

Diethyl [(2‐tetrahydropyranyloxy)methyl]phosphonate

intermediate: 33.63 g (0.2 mol) of diethyl hydroxymethylphosphonate

product: Diethyl [(2‐tetrahydropyranyloxy)methyl]phosphonate
α‐Hydroxy Ketones from the Oxidation of Enol Silyl Ethers with
m
‐Chloroperbenzoic Acid: 6‐Hydroxy‐ 3,5,5‐Trimethyl‐2‐Cyclohexen‐1‐one
Authors: Rubottom George M. , Gruber John M. , Juve Henrik D. , Charleson Dan A. 
Published: November 2003

Abstract

α‐Hydroxy ketones from the oxidation of enol silyl ethers with
m
‐chloroperbenzoic acid: 6‐hydroxy‐ 3,5,5‐trimethyl‐2‐cyclohexen‐1‐one

solvent: 11.25 mL (80.4 mmol) of freshly distilled diisopropylamine

reactant: 10.0 g (72.4 mmol) of freshly distilled isophorone

reactant: 17.5 mL (137.6 mmol) of freshly distilled chlorotrimethylsilane (TMSCL)

intermediate: 4,6,6‐trimethyl‐2‐trimethylsiloxycyclohexa‐1,3‐diene

solvent: 3–5 mL of petroleum ether

product: 6‐hydroxy‐3,5,5‐trimethyl‐2‐cyclohexen‐1‐one
Ring Expansion and Cleavage of Succinoin Derivatives: Spiro[4.5]Decane‐1,4‐dione and Ethyl 4‐Cyclohexyl‐4‐Oxobutanoate
Authors: Nakamura Eiichi , Kuwajima Isao 
Published: November 2003

Abstract

Ring expansion and cleavage of succinoin derivatives: spiro[4.5]decane‐1,4‐dione and ethyl 4‐cyclohexyl‐4‐oxobutanoate

reactant: cyclohexanone diethyl ketal (6.88 g, 40 mmol)

product: spiro[4.5]decane‐1,4‐dione

product: Ethyl 4‐cyclohexyl‐4‐oxobutanoate (4)

reactant: 1,2‐Bis(trimethylsiloxy)cyclobut‐1‐ene

intermediate: 2‐(1‐ethoxycyclohexyl)‐2‐(trimethylsiloxy)cyclobutanone

intermediate: silyl ether 3
4‐Nitroindole
Authors: Bergman Jan , Sand Peter 
Published: November 2003

Abstract

4‐Nitroindole

intermediate: 20.8 g (0.10 mol) of ethyl N‐(2‐methyl‐3‐nitrophenyl)formimidate in 75 mL of dry dimethyl sulfoxide

product: 4‐nitroindole
Allylcarbamates by the Aza‐ene Reaction: Methyl
N
‐(2‐Methyl‐2‐Butenyl)Carbamate
Authors: Kresze Günter , Braxmeier Hans , Münsterer Heribert 
Published: November 2003

Abstract

Allylcarbamates by the aza‐ene reaction: methyl
N
‐(2‐methyl‐2‐butenyl)carbamate

intermediate: Methyl N,N‐dichlorocarbamate.

intermediate: N,N‐Bis(methoxycarbonyl)sulfur diimide.

product: Methyl N‐(2‐methyl‐2‐butenyl)carbamate.
Asymmetric Syntheses Using the
SAMP
‐/
RAMP
‐Hydrazone Method: (
S
)‐(+)‐4‐Methyl‐3‐Heptanone
Authors: Enders Dieter , Kipphardt Helmut , Fey Peter 
Published: November 2003

Abstract

Asymmetric syntheses using the SAMP‐/RAMP‐hydrazone method: (
S
)‐(+)‐4‐methyl‐3‐heptanone

intermediate: SAMP‐hydrazone (S)‐2

intermediate: (S)‐(+)‐4‐Methyl‐3‐heptanone SAMP hydrazone [(ZSS)‐3]

product: (S)‐(+)‐4‐Methyl‐3‐heptanone [(S)‐4]

byproduct: nitrosamine (S)‐5
1‐Deoxy‐2,3,4,6‐Tetra‐
O
‐Acetyl‐1‐(2‐Cyanoethyl)‐α‐
D
‐Glucopyranose
Authors: Giese Bernd , Dupuis J. , Nix Marianne 
Published: November 2003

Abstract

1‐Deoxy‐2,3,4,6‐tetra‐
O
‐acetyl‐1‐(2‐cyanoethyl)‐α‐
D
‐glucopyranose

product: 1‐deoxy‐2,3,4,6‐tetra‐
O
‐acetyl‐1‐(2‐cyanoethyl)‐α‐
D
‐glucopyranose

byproduct: tetra‐
O
‐acetyl‐1,5‐anhydroglucitol

byproduct: 1‐deoxy‐2,3,4,6‐tetra‐
O
‐acetyl‐1‐(2‐cyanoethyl)‐β‐
D
‐glucopyranose
6‐Bromo‐6‐deoxy Hexose Derivatives by Ring Opening of Benzylidene Acetals with
N
‐Bromosuccinimide: Methyl 4‐
O
‐Benzoyl‐6‐bromo‐6‐deoxy‐α‐D‐Glucopyranoside
Authors: Hanessian S. 
Published: November 2003

Abstract

6‐Bromo‐6‐deoxy hexose derivatives by ring opening of benzylidene acetals with
N
‐bromosuccinimide: methyl 4‐
O
‐benzoyl‐6‐bromo‐6‐deoxy‐α‐D‐glucopyranoside

product: Methyl 4‐O‐benzoyl‐6‐bromo‐6‐deoxy‐α‐D‐glucopyranoside

reactant: 20.5 g (72.61 mmol) of methyl 4,6‐O‐benzylidene‐α‐D‐glucopyranoside
Ethyl (
E,Z
)‐2,4‐Decadienoate
Authors: Tsuboi S. , Masuda T. , Mimura S. , Takeda A. 
Published: November 2003

Abstract

Ethyl (
E,Z
)‐2,4‐decadienoate

intermediate: Ethyl 3,4‐decadienoate (1)

product: Ethyl (E,Z)‐2,4‐decadienoate (2)
tert
‐Butyl Acetothioacetate and Its Use in Synthesis: 3‐Acetyl‐4‐hydroxy‐5,5‐dimethylfuran‐2(4
H
)‐one
Authors: Fox Christina M. J. , Ley Steven V. 
Published: November 2003

Abstract

tert
‐Butyl acetothioacetate and its use in synthesis: 3‐Acetyl‐4‐hydroxy‐5,5‐dimethylfuran‐2(4
H
)‐one

intermediate:
S
‐
tert
‐butyl 3‐oxobutanthioate

intermediate: 1‐Carbomethoxy‐1‐methylethyl 3‐oxobutanoate.

product: 3‐Acetyl‐4‐hydroxy‐5,5‐dimethylfuran‐2(5H)‐one.
(±)‐
trans
‐2‐(Phenylsulfonyl)‐3‐phenyloxaziridine
Authors: Vishwakarma Lal C. , Stringer Orum D. , Davis Franklin A. 
Published: November 2003

Abstract

(±)‐
trans
‐2‐(phenylsulfonyl)‐3‐phenyloxaziridine

intermediate: N‐Benzylidenebenzenesulfonamide.

product: (±)‐trans‐2‐(Phenylsulfonyl)‐3‐phenyloxaziridine.

product: R = Ph, Ar = 3NO2Ph

product: R = Ph, Ar = 4NO2Ph

product: R = Me, Ar = Ph

product: R = PhCH2, Ar = Ph
Enantiomeric (S)‐(+)‐ and (R)‐(−)‐1,1′‐Binaphthyl‐2,2′‐Diyl Hydrogen Phosphate
Authors: Jacques J. , Fouquey C. 
Published: November 2003

AbstractEnantiomeric (S)‐(+)‐ and (R)‐(−)‐1,1′‐binaphthyl‐2,2′‐diyl hydrogen phosphateintermediate: (±)‐binaphthylphosphoric acidintermediate: (S)‐(+)‐ and (R)‐(−)‐BNP acidintermediate: (S)‐(+)‐BNP acidproduct: (−)‐BNP acidreactant: (+)‐cinchonine (Aldrich Chemical Company, Inc.)
(
R
)‐(+)‐1,1′‐Binaphthalene‐2,2′‐diol
Authors: Truesdale Larry K. 
Published: November 2003

Abstract

(
R
)‐(+)‐1,1′‐binaphthalene‐2,2′‐diol

intermediate: (R)‐(−)‐Methyl 1,1′‐binaphthyl‐2,2′‐diylphosphate.

reactant: 20.0 g (57.4 mmol) of (R)‐(−)‐1,1′‐binaphthyl‐2,2′‐diyl hydrogen phosphate

product: (R)‐(+)‐1,1′‐binaphthalene‐2,2′‐diol
(
S
)‐
N,N
‐Dimethyl‐
N
′‐(1‐
tert
‐Butoxy‐3‐Methyl‐2‐Butyl)Formamidine
Authors: Dickman Daniel A. , Boes Michael , Meyers Albert I. 
Published: November 2003

Abstract

(
S
)‐
N,N
‐dimethyl‐
N
′‐(1‐
tert
‐butoxy‐3‐methyl‐2‐butyl)formamidine

intermediate: N‐formyl‐O‐tert‐butylvalinol (1)

product: (S)‐N,N‐dimethyl‐N′‐(1‐tert‐butoxy‐3‐methyl‐2‐butyl)formamidine
2‐(Phenylsulfonyl)‐1,3‐cyclohexadiene
Authors: Bäckvall Jan‐E. , Juntunen Seppo K. , Andell Ove S. 
Published: November 2003

Abstract

2‐(Phenylsulfonyl)‐1,3‐cyclohexadiene

intermediate: trans‐3‐(phenylsulfonyl)‐4‐(chloromercuri)cyclohexene

product: 2‐(phenylsulfonyl)‐1,3‐cyclohexadiene
Domino
D
iels–
A
lder Reaction: 3,3a,3b,4,6a,7a‐Hexahydro‐3,4,7‐metheno‐7
H
‐cyclopenta[
a
]pentalene‐7,8‐dicarboxylic Acid
Authors: Taylor Richard T. , Pelter Michael W. , Paquette Leo A. 
Published: November 2003

Abstract

Domino Diels–Alder Reaction: 3,3a,3b,4,6a,7a‐hexahydro‐3,4,7‐metheno‐7
H
‐cyclopenta[
a
]pentalene‐7,8‐dicarboxylic acid

product: 3,3a,3b,4,6a,7a‐Hexahydro‐3,4,7‐metheno‐7H‐cyclopenta[a]pentalene‐7,8‐dicarboxylic acid