bluuebunny/crossref_metadata_2025_split huggingface dataset:
Aldehydes by Oxidation of Terminal Olefins with Chromyl Chloride: 2,4,4‐Trimethylpentanal
Authors: Freeman Fillmore , DuBois Richard H. , McLaughlin Thomas G. 
Published: November 2003

Abstract

Aldehydes by oxidation of terminal olefins with chromyl chloride: 2,4,4‐trimethylpentanal

catalyst: 158 g. (1.02 moles) of freshly distilled chromyl chloride

product: 2,4,4‐trimethylpentanal

product: 4,4‐Dimethyl‐2‐neopentylpentanal

product: 2‐Phenylpropanal

product: Diphenylacetaldehyde
Aldehydes from Acid Chlorides by Modified
R
osenmund Reduction: 3,4,5‐Trimethoxybenzaldehyde
Authors: Rachlin A. I. , Gurien H. , Wagner D. P. 
Published: November 2003

Abstract

Aldehydes from acid chlorides by modified Rosenmund reduction: 3,4,5‐trimethoxybenzaldehyde

product: 3,4,5‐trimethoxybenzaldehyde

product: 3,4‐dimethylbenzaldehyde

product: 3‐benzyloxy‐4,5‐dimethoxybenzaldehyde

product: 3‐methoxy‐4‐nitrobenzaldehyde
Aldehydes from Aromatic Nitriles: 4‐Formylbenzenesulfonamide
Authors: van Es T. , Staskun B. 
Published: November 2003

Abstract

Aldehydes from aromatic nitriles: 4‐formylbenzenesulfonamide

product: 4‐formylbenzenesulfonamide

product: C
6
H
5
CHO

product: 4‐ClC
6
H
4
CHO

product: 4‐CH
3
OC
6
H
4
CHO

product: 2‐C
10
H
7
CHO

product: C
6
H
5
CHO

product: 2‐CH
3
C
6
H
4
CHO

product: 2‐ClC
6
H
4
CHO

product: 2‐CH
3
OC
6
H
4
CHO

product: 2,6‐(CH
3
O)
2
C
6
H
3
CHO

product: C
6
H
5
CHCHCHO
Aldehydes from 2‐Benzyl‐4,4,6‐Trimethyl‐5,6‐Dihydro‐1,3(4
H
)‐Oxazine: 1‐Phenylcyclopentanecarboxaldehyde
Authors: Politzer Ieva R. , Meyers A. I. 
Published: November 2003

Abstract

Aldehydes from 2‐benzyl‐4,4,6‐trimethyl‐5,6‐dihydro‐1,3(4
H
)‐oxazine: 1‐phenylcyclopentanecarboxaldehyde

reactant: 21.7 g. (0.100 mole) of 2‐benzyl‐4,4,6‐trimethyl‐5,6‐dihydro‐1,3(4
H
)‐oxazine

reactant: 1,4‐Dibromobutane (23.8 g., 0.110 mole)

intermediate: 2‐(1‐phenylcyclopentyl)‐4,4,6‐trimethyl‐5,6‐dihydro‐1,3(4
H
)‐oxazine

intermediate: 2‐(1‐
Phenylcyclopentyl
)‐4,4,6‐
trimethyltetrahydro
‐1,3‐
oxazine

solvent: 150‐ml. portions of petroleum ether

product: 1‐phenylcyclopentanecarboxaldehyde
Amines from Mixed Carboxylic‐Carbonic Anhydrides: 1‐Phenylcyclopentylamine
Authors: Kaiser Carl , Weinstock Joseph 
Published: November 2003

Abstract

Amines from Mixed Carboxylic‐Carbonic Anhydrides: 1‐Phenylcyclopentylamine

reactant: 38.0 g. (0.200 mole) of 1‐phenylcyclopentanecarboxylic acid

product: 1‐phenylcyclopentylamine
Aziridines from β‐Iodocarbamates: 1,2,3,4‐Tetrahydronaphthalene(1,2)imine
Authors: Heathcock C. H. , Hassner A. 
Published: November 2003

Abstract

Aziridines from β‐iodocarbamates: 1,2,3,4‐tetrahydronaphthalene(1,2)imine

product: 1,2,3,4‐Tetrahydronaphthalene(1,2)imine
3‐Chlorocyclobutanecarboxylic Acid
Authors: Lampman Gary M. , Aumiller James C. 
Published: November 2003

Abstract

3‐Chlorocyclobutanecarboxylic acid

reactant: 172.8 g. (1.200 moles) of 1,1‐cyclobutanedicarboxylic acid

byproduct: cyclobutanecarboxylic acid

product: 3‐chlorocyclobutanecarboxylic acid
Ethyl Pyrrole‐2‐Carboxylate
Authors: Bailey Denis M. , Johnson Robert E. , Albertson Noel F. 
Published: November 2003

Abstract

Ethyl pyrrole‐2‐carboxylate

intermediate: 2‐
Pyrrolyl trichloromethyl ketone

product: ethyl pyrrole‐2‐carboxylate
Hydrogenation of Aromatic Nuclei: 1‐Decalol
Authors: Meyers A. I. , Beverung W. N. , Gault R. 
Published: November 2003

Abstract

Hydrogenation of aromatic nuclei: 1‐Decalol

product:
cis,cis
‐1‐decalol

product: 2‐Decalol

product:
cis
‐2‐Methylhexahydrobenzofuran

product:
cis
‐2,2‐Dimethylhexahydrobenzofuran

product: 3‐Hydroxycyclohexanecarboxylic acid

product: 4‐Methoxycyclohexanol

product: 1,4‐Cyclohexanediol

product: 1,3‐Cyclohexanediol
4‐Phenyl‐1,2,4‐Triazoline‐3,5‐Dione
Authors: Cookson R. C. , Gupte S. S. , Stevens I. D. R. , Watts C. T. 
Published: November 2003

Abstract

4‐Phenyl‐1,2,4‐triazoline‐3,5‐dione

intermediate: 52 g. (0.50 mole) of ethyl hydrazinecarboxylate in 550 ml. of dry benzene

intermediate: 4‐phenyl‐1‐carbethoxysemicarbazide

intermediate: 4‐phenylurazole

product: 4‐(4‐nitrophenyl)urazole

product: 4‐
tert
‐butylurazole

product: 4‐Benzalaminourazole

product: 4‐benzalamino‐1,2,4‐triazoline‐3,5‐dione

product: 4‐Phenyl‐1,2,4‐triazoline‐3,5‐dione
Phenylation with Diphenyliodonium Chloride: 1‐Phenyl‐2,4‐Pentanedione
Authors: Hampton K. Gerald , Harris Thomas M. , Hauser Charles R. 
Published: November 2003

Abstract

Phenylation with diphenyliodonium chloride: 1‐phenyl‐2,4‐pentanedione

reactant: 40.0 g. (0.400 mole) of 2,4‐pentanedione

product: 1‐phenyl‐2,4‐pentanedione

byproduct: iodobenzene

product: 1‐phenyl‐1,3‐butanedione

product: 2,4‐heptanedione

product: 2,4‐nonanedione

product: 2,4‐tridecanedione

product: 3,5‐heptanedione

product: 1‐(4‐chlorophenyl)‐2,4‐pentanedione

product: 4‐(4‐methylphenyl)‐1‐phenyl‐1,3‐butanedione

product: 1‐(4‐methylphenyl)‐2,4‐nonanedione
1,2,3,4‐Tetrahydro‐β‐Carboline
Authors: Ho Beng T. , Walker K. E. 
Published: November 2003

Abstract

1,2,3,4‐Tetrahydro‐β‐carboline

reactant: 25 g. (0.13 mole) of tryptamine hydrochloride

product: 1,2,3,4‐tetrahydro‐β‐carboline
Thiophenols from Phenols: 2‐Naphthalenethiol
Authors: Newman Melvin S. , Hetzel Frederick W. 
Published: November 2003

AbstractThiophenols from phenols: 2‐naphthalenethiolreactant: 21.6 g. (0.150 mole) of 2‐naphtholreactant: 24.8 g. (0.201 mole) ofN,N‐dimethylthiocarbamyl chlorideintermediate:O‐2‐naphthyl dimethylthiocarbamateproduct: 2‐naphthalenethiol
Aldehydes from Primary Alcohols by Oxidation with Chromium Trioxide: Heptanal
Authors: Collins J. C. , Hess W. W. 
Published: November 2003

Abstract

Aldehydes from primary alcohols by oxidation with chromium trioxide: heptanal

intermediate: dipyridine chromium(VI) oxide

reactant: 5.8 g. (0.050 mole) of 1‐heptanol

product: heptanal

product: 2‐methoxybenzaldehyde

product: 4‐nitrobenzaldehyde
3‐Butyl‐2‐methylhept‐1‐en‐3‐ol
Authors: Pearce P. J. , Richards D. H. , Scilly N. F. 
Published: November 2003

Abstract

3‐Butyl‐2‐methylhept‐1‐en‐3‐ol

product: 3‐butyl‐2‐methyl‐1‐hepten‐3‐ol

solvent: petroleum ether

product: 3‐Pentanol

product: Benzhydrol

product: Tri‐
n
‐butyl carbinol

product: 5‐Nonanol

product: 1‐Penten‐3‐ol

product: 3‐Methyl‐4‐heptanol
Formation and Photochemical
W
olff Rearrangement of Cyclic α‐Diazo Ketones:
D
‐Norandrost‐5‐en‐3β‐ol‐16‐Carboxylic Acids
Authors: Wheeler Thomas N. , Meinwald J. 
Published: November 2003

Abstract

Formation and photochemical Wolff rearrangement of cyclic α‐diazo ketones:
D
‐norandrost‐5‐en‐3β‐ol‐16‐carboxylic acids

intermediate: 16‐
Oximinoandrost
‐5‐
en
‐3β‐
ol
‐17‐
one

intermediate: 7.50 g. (0.0239 mole) of 16‐diazoandrost‐5‐en‐3β‐ol‐17‐one

product:
D
‐norandrost‐5‐en‐3β‐ol‐16α‐carboxylic acid

product: methyl
D
‐norandrost‐5‐en‐3β‐ol‐16β‐carboxylate
Hydrogenolysis of Carbon‐Halogen Bonds with Chromium(II)‐en Perchlorate: Naphthalene from 1‐Bromonaphthalene
Authors: Wade Ruth S. , Castro C. E. 
Published: November 2003

Abstract

Hydrogenolysis of carbon‐halogen bonds with chromium(II)‐en perchlorate: naphthalene from 1‐bromonaphthalene

reactant: 6.01 g. (0.100 mole) of ethylenediamine

reactant: 1.66 g. (0.00802 mole) of 1‐bromonaphthalene

product: naphthalene
Macrocyclic Polyethers: Dibenzo‐18‐crown‐6 Polyether and Dicyclohexyl‐18‐crown‐6 Polyether
Authors: Pedersen Charles J. 
Published: November 2003

Abstract

Macrocyclic polyethers: Dibenzo‐18‐crown‐6 polyether and dicyclohexyl‐18‐crown‐6 polyether

reactant: 222 g. (1.55 moles) of bis(2‐chloroethyl) ether

product: Dibenzo‐18‐crown‐6 polyether

product: dicyclohexyl‐18‐crown‐6 polyethers

solvent: petroleum ether (b.p. 30–60°, approximately 200 ml. was required)

solvent: dichloromethane–petroleum ether

intermediate: complex of potassium acetate with isomer B of dicyclohexyl‐18‐crown‐6 polyether
2‐Methyl‐2‐Nitrosopropane and its Dimer
Authors: Calder A. , Forrester A. R. , Hepburn S. P. 
Published: November 2003

Abstract

2‐Methyl‐2‐nitrosopropane and its dimer

product: 2‐methyl‐2‐nitropropane

intermediate: N‐tert‐
Butylhydroxylamine

intermediate: 2‐
Methyl
‐2‐
nitrosopropane
Reaction of Aryl Halides with π‐Allylnickel Halides: Methallylbenzene
Authors: Semmelhack Martin F. , Helquist Paul M. 
Published: November 2003

AbstractReaction of aryl halides with π‐allylnickel halides: methallylbenzenereactant: 50.8 g. (38.5 ml., 0.298 mole) of nickel carbonylsolvent: 250 ml. of petroleum etherproduct: methallylbenzenereactant: Methallyl bromideintermediate: π‐methallylnickel bromidebyproduct: 1% 2,5‐dimethyl‐1,5‐hexadienebyproduct: biphenylproduct: β,β‐dimethylstyrene
Substitution of Aryl Halides with Copper(
I
) Acetylides: 2‐Phenylfuro[3,2‐
b
]Pyridine
Authors: Owsley D. C. , Castro C. E. 
Published: November 2003

Abstract

Substitution of aryl halides with copper(I) acetylides: 2‐phenylfuro[3,2‐
b
]pyridine

reactant: copper(I) phenylacetylide

product: 2‐
Phenylfuro
[3,2‐b]
pyridine
2‐Acetyl‐6‐Methoxynaphthalene
Authors: Arsenijevic L. , Arsenijevic V. , Horeau A. , Jacques J. 
Published: November 2003

Abstract

2‐acetyl‐6‐methoxynaphthalene

product: 2‐acetyl‐6‐methoxynaphthalene

reactant: 2‐Methoxynaphthalene (Matheson, Coleman and Bell)
3,5‐Dinitrobenzaldehyde
Authors: Siggins J. E. , Larsen A. A. , Ackerman J. H. , Carabateas C. D. 
Published: November 2003

Abstract

3,5‐Dinitrobenzaldehyde

reactant: 115.0 g. (0.4989 mole) of 3,5‐dinitrobenzoyl chloride

solvent: 500 ml. of dry diglyme

product: 3,5‐dinitrobenzaldehyde
β‐Hydroxy Esters from Ethyl Acetate and Aldehydes or Ketones: Ethyl 1‐Hydroxycyclohexylacetate
Authors: Rathke Michael W. 
Published: November 2003

Abstract

β‐Hydroxy Esters from Ethyl Acetate and Aldehydes or Ketones: Ethyl 1‐hydroxycyclohexylacetate

reactant: 42.2 g. (0.263 mole) of hexamethyldisilazane

byproduct: hexamethyldisiloxane

product: Ethyl 1‐hydroxycyclohexylacetate
2,2‐(Trimethylenedithio)Cyclohexanone
Authors: Woodward R. B. , Pachter I. J. , Scheinbaum M. L. 
Published: November 2003

Abstract

2,2‐(Trimethylenedithio)cyclohexanone

intermediate: 1‐
Pyrrolidinocyclohexene

product: 2,2‐
(Trimethylenedithio)cyclohexanone

reactant: Trimethylene dithiotosylate
N
‐Alkylindoles from the Alkylation of Sodium Indolide in Hexamethylphosphoric Triamide: 1‐Benzylindole
Authors: Rubottom George M. , Chabala John C. 
Published: November 2003

Abstract

N
‐alkylindoles from the alkylation of sodium indolide in hexamethylphosphoric triamide: 1‐benzylindole

product: 1‐benzylindole
Preparation of Vinyl Trifluoromethanesulfonates: 3‐Methyl‐2‐buten‐2‐yl Triflate
Authors: Stang Peter J. , Dueber Thomas E. 
Published: November 2003

Abstract

Preparation of Vinyl Trifluoromethanesulfonates: 3‐Methyl‐2‐buten‐2‐yl Triflate

intermediate: trifluoromethanesulfonic anhydride

reactant: 2.78 g. (0.0352 mole) of anhydrous pyridine

solvent: 10 ml. of anhydrous
n
‐pentane

product: 3‐methyl‐2‐buten‐2‐yl triflate

byproduct: 3‐methyl‐1‐buten‐2‐yl triflate

product: CH
2
C(CH
3
)OSO
2
CF
3

product:
cis
and
trans
C
2
H
5
CHC(C
2
H
5
)OSO
2
CF
3

product: CH
2
C(OSO
2
CF
3
)C(CH
3
)
3

product: CH
2
C(C
6
H
5
)OSO
2
CF
3

product: CH
2
C(OSO
2
CF
3
)CH
2
(CH
2
)
2
CH
3

product: CH
2
C(OSO
2
CF
3
)CH(CH
3
)
2

product: C
6
H
5
C(CH
3
)C(CH
3
)OSO
2
CF
3
(
cis
, 18%;
trans
, 51%) + C
6
H
5
CH(CH
3
)C(OSO
2
CF
3
)CH
2
(31%)

product: C
6
H
5
C(CH
3
)C(CH
3
)OSO
2
CF
3
(
trans
, 80%;
cis
, 20%)

product: (CH
3
)
2
CC(CH
3
)OSO
2
CF
3
(
1
, 70%) + (CH
3
)
2
CHC(OSO
2
CF
3
)CH
2
(
2
, 30%)

product:
1
(90%) +
2
(10%)
Macrocyclic Diimines: 1,10‐Diazacycloöctadecane
Authors: Park Chung Ho , Simmons Howard E. 
Published: November 2003

Abstract

Macrocyclic diimines: 1,10‐Diazacycloöctadecane

intermediate: 1,10‐diazacycloöctadecane‐2,9‐dione

product: 1,10‐diazacycloöctadecane
Tri‐
tert
‐Butylcyclopropenyl Tetrafluoroborate
Authors: Ciabattoni J. , Nathan E. C. , Feiring A. E. , Kocienski P. J. 
Published: November 2003

Abstract

Tri‐
tert
‐Butylcyclopropenyl tetrafluoroborate

reactant: 74.6 g. (0.700 mole) of 1‐chloro‐2,2‐dimethylpropane

reactant: 71.7 g. (0.533 mole) of
tert
‐butylacetyl chloride

intermediate: dineopentyl ketone

intermediate: α,α′‐
Dibromodineopentyl ketone

intermediate: 20.0 g. (0.120 mole) of di‐
tert
‐butylcyclopropenone

product: tri‐
tert
‐butylcyclopropenyl tetrafluoroborate
Addition of Organolithium Reagents to Allyl Alcohol: 2‐Methyl‐1‐Hexanol
Authors: Crandall J. K. , Rojas A. C. 
Published: November 2003

AbstractAddition of Organolithium Reagents to Allyl Alcohol: 2‐Methyl‐1‐Hexanolreactant: 7.25 g. (0.125 mole) of 2‐propen‐1‐olreactant: 1.16 g. (0.0100 mole) ofN,N,N′,N′‐tetramethyl‐1,2‐ethanediamineproduct: 2‐methyl‐1‐hexanol
Alkenes
via
H
ofmann Elimination: Use of Ion‐Exchange Resin for Preparation of Quaternary Ammonium Hydroxides: Diphenylmethyl Vinyl Ether
Authors: Kaiser Carl , Weinstock Joseph 
Published: November 2003

Abstract

Alkenes
via
Hofmann elimination: use of ion‐exchange resin for preparation of quaternary ammonium hydroxides: diphenylmethyl vinyl ether

product: diphenylmethyl vinyl ether

reactant: 2‐(diphenylmethoxy)‐
N,N
‐dimethylethylamine, b.p. 150–165° (2 mm.),G. Rieveschl, Jr., (to Parke Davis and Company), U.S. Pat. 2,421,714 (1947) [Chem. Abstr., 41, 5550 h (1947)]. obtained from Searle Chemicals, Inc., or from the hydrochloride, m.p. 161–162°, which is available commercially from Gane's Chemical Works, Inc., New York, New York, under the generic name, diphenhydramine

intermediate: 2‐(diphenylmethoxy)‐
N,N
‐dimethylethylamine methiodide
3‐(4‐Chlorophenyl)‐5‐(4‐Methoxyphenyl)Isoxazole
Authors: Perkins Matilda , Beam Charles F. , Dyer Morgan C. D. , Hauser Charles R. 
Published: November 2003

Abstract

3‐(4‐Chlorophenyl)‐5‐(4‐methoxyphenyl)isoxazole

reactant: 16.96 g. (0.1000 mole) of 4‐chloroacetophenone oxime

product: 3‐(4‐chlorophenyl)‐5‐(4‐methoxyphenyl)isoxazole
4,4′‐Dimethyl‐1,1′‐Biphenyl
Authors: Elsom L. F. , McKillop Alexander , Taylor Edward C. 
Published: November 2003

Abstract

4,4′‐Dimethyl‐1,1′‐biphenyl

reactant: 42.7 g. (30.5 ml., 0.250 mole) of 4‐bromotoluene

intermediate: (4‐methylphenyl)magnesium bromide

product: 4,4′‐dimethyl‐1,1′‐biphenyl

product: biphenyl

product: 4,4′‐dimethoxy‐1,1′‐biphenyl

product: 3,3′‐dimethyl‐1,1′‐biphenyl

product: 3,3′,4,4′‐tetramethyl‐1,1′‐biphenyl

product: 4,4′‐dichloro‐1,1′‐biphenyl

product: 4,4′‐difluoro‐1,1′‐biphenyl
Free‐Radical Cyclization: Ethyl 1‐Cyano‐2‐Methylcyclohexanecarboxylate
Authors: Julia Marc , Maumy Michel 
Published: November 2003

Abstract

Free‐radical cyclization: ethyl 1‐cyano‐2‐methylcyclohexanecarboxylate

intermediate: (
E
)‐4‐hexen‐1‐yl
p
‐toluenesulfonate

solvent: 400 ml. of anhydrous
N,N
‐dimethylformamide

reactant: 68 g. (0.60 mole) of ethyl cyanoacetate

intermediate: ethyl (
E
)‐2‐cyano‐6‐octenoate

product: ethyl 1‐cyano‐2‐methylcyclohexanecarboxylate
Phase‐Transfer Alkylation of Nitriles: 2‐Phenylbutyronitrile
Authors: Makosza M. , Jończyk A. 
Published: November 2003

Abstract

Phase‐transfer alkylation of nitriles: 2‐phenylbutyronitrile

product: 2‐phenylbutyronitrile

byproduct: α‐phenylcinnamonitrile

product: (C
6
H
5
)
2
CHCH(C
6
H
5
)CN

product: (C
6
H
5
)
2
C(CH
2
CH
2
Br)CN
Secondary and Tertiary Alkyl Ketones from Carboxylic Acid Chlorides and Lithium Phenylthio(Alkyl)Cuprate Reagents:
tert
‐Butyl Phenyl Ketone
Authors: Posner Gary H. , Whitten Charles E. 
Published: November 2003

Abstract

Secondary and tertiary alkyl ketones from carboxylic acid chlorides and lithium phenylthio(alkyl)cuprate reagents:
tert
‐butyl phenyl ketone

reactant: 8.81 g. (0.0801 mole) of freshly distilled thiophenol

reactant: 2.81 g. (0.0200 mole) of freshly distilled benzoyl chloride

product:
tert
‐butyl phenyl ketone

byproduct:
tert
‐butyl benzoate (from lithium
tert
‐butoxide;)
Acylamidoalkyl Acetophenones from Substituted Phenethylamines: 2‐(2‐Acetamidoethyl)‐4,5‐Dimethoxyacetophenone
Authors: Brossi A. , Dolan L. A. , Teitel S. 
Published: November 2003

Abstract

Acylamidoalkyl acetophenones from substituted phenethylamines: 2‐(2‐acetamidoethyl)‐4,5‐dimethoxyacetophenone

reactant: 54.0 g. (0.243 mole) of
N
‐acetylhomoveratrylamine

intermediate: 6,7‐dimethoxy‐1‐methyl‐3,4‐dihydroisoquinoline dichlorophosphate

intermediate: 2‐
Acetyl
‐6,7‐
dimethoxy
‐1‐
methylene
‐1,2,3,4‐
tetrahydroisoquinoline

intermediate: 2‐(2‐
Acetamidoethyl
)‐4,5‐
dimethoxyacetophenone

product: R
1
= OCH
3
, R
2
= R
3
= H

product: R
1
, R
2
= OCH
2
O, R
3
= H

product: R
1
= R
2
= R
3
= OCH
3
3‐Alkylated and 3‐Acylated Indoles from a Common Precursor: 3‐Benzylindole and 3‐Benzoylindole
Authors: Stütz P. , Stadler P. A. 
Published: November 2003

Abstract

3‐Alkylated and 3‐acylated indoles from a common precursor: 3‐benzylindole and 3‐benzoylindole

intermediate: 2‐phenyl‐1,3‐dithiane

intermediate: 2‐methylthio‐2‐phenyl‐1,3‐dithiane

intermediate: 3‐(2‐phenyl‐1,3‐dithian‐2‐yl)‐1
H
‐indole

product: 3‐benzoylindole

product: 3‐benzylindole
Carboxylation of Aromatic Compounds: Ferrocenecarboxylic Acid
Authors: Reeves Perry C. 
Published: November 2003

Abstract

Carboxylation of aromatic compounds: ferrocenecarboxylic acid

intermediate: (2‐chlorobenzoyl)ferrocene

product: ferrocenecarboxylic acid

product: carboxycyclopentadienyltricarbonylmanganese

product: biphenyl‐4‐carboxylic acid

product: 3,4‐dimethylbenzoic acid

product: 2,4,6‐trimethylbenzoic acid

product: 3,4‐dimethoxybenzoic acid

product: 2,4‐dimethoxybenzoic acid
Chain Elongation of Alkenes
via gem
‐Dihalocyclopropanes: 2‐Bromo‐3,3‐diphenyl‐2‐propen‐1‐yl Acetate
Authors: Sandler Stanely R. 
Published: November 2003

Abstract

Chain elongation of alkenes
via gem
‐dihalocyclopropanes: 2‐bromo‐3,3‐diphenyl‐2‐propen‐1‐yl acetate

product: 2‐Bromo‐3,3‐diphenyl‐2‐propen‐1‐yl acetate

intermediate: 17.6 g. (0.0500 mole) of 1,1‐dibromo‐2,2‐diphenylcyclopropane
Conversion of Nitro to Carbonyl by Ozonolysis of Nitronates: 2,5‐Heptanedione
Authors: McMurry John E. , Melton Jack 
Published: November 2003

Abstract

Conversion of nitro to carbonyl by ozonolysis of nitronates: 2,5‐heptanedione

intermediate: 5‐nitroheptan‐2‐one

product: 2,5‐heptanedione
Demethylation of Methyl Aryl Ethers: 4‐Ethoxy‐3‐Hydroxybenzaldehyde
Authors: Ireland Robert E. , Walba David M. 
Published: November 2003

Abstract

Demethylation of methyl aryl ethers: 4‐ethoxy‐3‐hydroxybenzaldehyde

reactant: 5.0 g. (0.028 mole) of 4‐ethoxy‐3‐methoxybenzaldehyde

reactant: 5.0 ml. (0.029 mole) of diphenylphosphine

intermediate: 5.0 g. (0.022 mole) of 4‐ethoxy‐3‐methoxybenzaldehyde ethylene acetal

product: 4‐hydroxy‐3‐ethoxybenzaldehyde
Indoles from Anilines: Ethyl 2‐Methylindole‐5‐Carboxylate
Authors: Gassman P. G. , van Bergen T. J. 
Published: November 2003

Abstract

Indoles from anilines: ethyl 2‐methylindole‐5‐carboxylate

intermediate: methylthio‐2‐propanone

intermediate: ethyl 2‐methyl‐3‐methylthioindole‐5‐carboxylate

product: ethyl 2‐methylindole‐5‐carboxylate
Peptide Syntheses UsingN‐Ethyl‐5‐Phenylisoxazolium‐3′‐Sulfonate: Carbobenzoxy‐L‐Asparaginyl‐L‐Leucine Methyl Ester andN‐Carbobenzoxy‐3‐Hydroxy‐L‐Prolylglycylglycine Ethyl Ester
Authors: Woodward R. B. , Olofson R. A. 
Published: November 2003

AbstractPeptide syntheses usingN‐ethyl‐5‐phenylisoxazolium‐3′‐sulfonate: carbobenzoxy‐L‐asparaginyl‐L‐leucine methyl ester andN‐carbobenzoxy‐3‐hydroxy‐L‐prolylglycylglycine ethyl esterreactant: 2.024 g. (0.00800 mole) ofN‐ethyl‐5‐phenylisoxazolium‐3′‐sulfonatereactant: 810 mg. (0.00802 mole) of triethylaminereactant: 1.452 g. (0.00800 mole) ofL‐leucine methyl ester hydrochlorideproduct: carbobenzyloxy‐L‐asparaginyl‐L‐leucine methyl esterreactant: 796 mg. (0.00300 mole) ofN‐carbobenzyloxy‐3‐hydroxy‐L‐prolinereactant: 590 mg. (0.00300 mole) of glycylglycine ethyl ester hydrochlorideproduct:N‐carbobenzyloxy‐3‐hydroxy‐L‐prolylglycylglycine ethyl estersolvent: petroleum etherproduct: Z‐(Nε‐Z)‐Lys·Gly‐OEt[Glycine,N‐[N2,N6‐bis‐[(phenylmethoxy)carbonyl]‐L‐lysyl]‐, ethyl ester]product: Z‐Phe·Gly‐OEt[Glycine,N‐[N‐[(phenylmethoxy)‐carbonyl]‐L‐phenylalanyl]‐, ethyl ester]product: Z‐Phe·Leu‐OMe[L‐Leucine,N‐[N‐[(phenylmethoxy)‐carbonyl]‐L‐phenylalanyl]‐, methyl ester]product: Z‐Met·Gly·Gly‐OEt[Glycine,N‐[N‐[N‐(phenylmethoxy)carbonyl]‐L‐methionyl]glycyl‐, ethyl ester]product: Phth‐Gly·Gly‐OEt[Glycine,N‐[(1,3‐dihydro‐1,3‐dioxo‐2H‐isoindol‐2‐yl)acetyl]‐, ethyl ester]product: Z‐Gly·Gly·Tyr‐OMe[L‐Tyrosine,N‐[N‐[N‐[(phenylmethoxy)carbonyl]glycyl]glycyl]‐, methyl ester]product: Z‐Gly·DL‐Phe·Gly‐OEt[Glycine,N‐[N‐N‐[(phenylmethoxy)carbonyl]glycyl‐DL‐phenelalanyl]‐, ethyl ester]product: Z‐Gly·Gly·Gly‐OEt[Glycine,N‐[N‐[N‐[(phenylmethoxy)carbonyl]glycyl]glycyl]‐, ethyl ester]product: Z‐Gly‐NHBz[Carbamic acid, [2‐oxo‐2‐[(phenylmethyl)amino]ethyl]‐, phenylmethyl ester]product: Z‐Asp·Gly‐OEt [Glycine,N‐[N2‐[(phenylmethoxy)carbonyl]‐L‐asparaginyl]‐, ethyl ester]product: Z‐Gln·Val‐OMe[L‐Valine,N‐[N2‐[(phenylmethoxy)carbonyl]‐Lglutaminyl]‐, methyl ester]product: Z‐Gln·Tyr‐OMe[L‐Tyrosine,N‐[N2‐[(phenylmethoxy)carbonyl]‐L‐glutaminyl]‐, methyl ester]
Polymeric Carbodiimide.
M
offat Oxidation: 4‐
tert
‐Butylcyclohexanone
Authors: Weinshenker Ned M. , Shen Chah M. , Wong Jack Y. 
Published: November 2003

Abstract

Polymeric carbodiimide. Moffat oxidation: 4‐
tert
‐butylcyclohexanone

product: 4‐
tert
‐butylcyclohexanone
Trifluoroacetylation of Amines and Amino Acids under Neutral, Mild Conditions:
N
‐Trifluoroacetanilide and
N
‐Trifluoroacetyl‐L‐Tyrosine
Authors: Panetta C. A. 
Published: November 2003

Abstract

Trifluoroacetylation of amines and amino acids under neutral, mild conditions:
N
‐trifluoroacetanilide and
N
‐trifluoroacetyl‐L‐tyrosine

reactant: 21.5 g. (0.0998 mole) of 1,1,1‐trichloro‐3,3,3‐trifluoroacetone

product:
N
‐trifluoroacetanilide

product:
N
‐trifluoroacetyl‐
L
‐tyrosine

reactant: 35.0 g. (0.192 mole) of chloropentafluoroacetone (b.p. 7.8°; available from PCR, Inc., or Allied Chemical Corp.)

product: TFA‐Aniline

product: TFA‐
L
‐Valine

product: TFA‐
DL
‐Phenylalanine

product: TFA‐
L
‐Phenylalanine

product: TFA‐
L
‐Leucine

product: TFA‐
L
‐Tyrosine

product: TFA‐
L
‐Proline

product: TFA‐
DL
‐Alanine

product: TFA‐Glycylglycine

product: TFA‐
L
‐Prolyglycine, ethyl ester

product: TFA‐
L
‐Asparagine

product: TFA‐Dehydroabietylamine
2‐Adamantanecarbonitrile
Authors: Oldenziel O. H. , Wildeman J. , van Leusen A. M. 
Published: November 2003

Abstract

2‐adamantanecarbonitrile

solvent: petroleum ether

product: 2‐adamantanecarbonitrile

reactant:
p
‐tolylsulfonylmethyl isocyanide

product: 2‐adamantanecarboxylic acid
Bis[2,2,2‐trifluoro‐1‐phenyl‐1‐(trifluoromethyl) Ethoxy] Diphenyl Sulfurane
Authors: Martin J. C. , Arhart R. J. , Franz J. A. , Perozzi E. F. , Kaplan L. J. 
Published: November 2003

Abstract

Bis[2,2,2‐trifluoro‐1‐phenyl‐1‐(trifluoromethyl) ethoxy] diphenyl sulfurane

reactant: 100.0 g. (0.4098 mole) of 1,1,1,3,3,3‐hexafluoro‐2‐phenyl‐2‐propanol

intermediate: potassium 1,1,1,3,3,3‐hexafluoro‐2‐phenyl‐2‐propanolate

product:
Bis
[2,2,2‐
trifluoro
‐1‐
phenyl
‐1‐(
trifluoromethyl
)
ethoxy
]
diphenyl sulfurane
(
Z
)‐4‐Chloro‐4‐Hexenyl Trifluoroacetate
Authors: Peterson P. E. , Dunham M. 
Published: November 2003

Abstract

(
Z
)‐4‐chloro‐4‐hexenyl trifluoroacetate

reactant: 35.3 g. (50.0 ml., 0.882 mole) of precondensed propyne

reactant: 153.5 g. (0.975 mole) of 1‐bromo‐3‐chloropropane

intermediate: 6‐chloro‐2‐hexyne

product: 4‐chloro‐4‐hexenyl trifluoroacetate
Cyclopropenone
Authors: Breslow R. , Pecoraro J. , Sugimoto T. 
Published: November 2003

Abstract

Cyclopropenone

intermediate: 1‐bromo‐3‐chloro‐2,2‐dimethoxypropane (21.7 g., 0.100 mole)

intermediate: 3,3‐dimethoxycyclopropene

product: cyclopropenone
2,2,7,7,12,12,17,17‐Octamethyl‐21,22,23,24‐tetraoxaperhydroquaterene
Authors: Chastrette Maurice , Chastrette Francine , Sabadie Jean 
Published: November 2003

Abstract

2,2,7,7,12,12,17,17‐octamethyl‐21,22,23,24‐tetraoxaperhydroquaterene

intermediate: 2,2,7,7,12,12,17,17‐
Octamethyl
‐21,22,23,24‐
tetraoxaquaterene.

reactant: 27.2 g. (0.400 mole) of freshly distilled furan

catalyst: 57.3 g. (0.200 mole) of the lithium perchlorate–1,2‐dimethoxyethane complex

product: 2,2,7,7,12,12,17,17‐
Octamethyl
‐21,22,23,24‐
tetraoxaperhydroquaterene.