bluuebunny/crossref_metadata_2025_split huggingface dataset:
1,4‐Pentadiene
Authors: Benson R. E. , McKusick B. C. , Grummitt Oliver , Budewitz E. P. , Chudd C. C. 
Published: November 2003

Abstract

1,4‐Pentadiene

reactant: 658 g. (645 ml., 3.5 moles) of 1,5‐pentanediol diacetate

product: 1,4‐pentadiene

reactant: 200 g. (201 ml.) of redistilled paraldehyde

intermediate: α‐chloroethyl ethyl ether

intermediate: α,β‐dibromoethyl ethyl ether

reactant: 400 g. (287 ml., 3.31 moles) of allyl bromide

reactant: allylmagnesium bromide

intermediate: α‐allyl‐β‐bromoethyl ethyl ether

reactant: 76.5 g. (82 ml., 1 mole) of allyl chloride

reactant: allylmagnesium chloride
N,N‐Dimethylcyclohexylmethylamine
Authors: Cope Arthur C. , Ciganek Engelbert 
Published: November 2003

Abstract

N,N‐Dimethylcyclohexylmethylamine

intermediate: N,N‐dimethylcyclohexanecarboxamide

product: N,N‐dimethylcyclohexylmethylamine
2‐Mercapto‐4‐Amino‐5‐Carbethoxypyrimidine and 2‐Mercapto‐4‐Hydroxy‐5‐Cyanopyrimidine
Authors: Ulbricht T. L. V. , Okuda Takuo , Price Charles C. 
Published: November 2003

Abstract

2‐Mercapto‐4‐amino‐5‐carbethoxypyrimidine and 2‐mercapto‐4‐hydroxy‐5‐cyanopyrimidine

product:
2‐Mercapto‐4‐amino‐5‐carbethoxypyrimidine.

reactant: 169 g. (1 mole) of liquefied ethyl ethoxymethylenecyanoacetate

product:
2‐Mercapto‐4‐hydroxy‐5‐cyanopyrimidine.
3‐Bromoacetophenone
Authors: Pearson D. E. , Pope H. W. , Hargrove W. W. 
Published: November 2003

Abstract

3‐Bromoacetophenone

product: 3‐bromoacetophenone

product: 3‐bromopropiophenone

product: 3‐bromo‐4‐methylacetophenone

product: 3,4‐dibromoacetophenone

product: 3‐bromo‐4‐
tert
‐butylacetophenone

product: 3,5‐dibromo‐4‐methylacetophenone

product: 3‐bromobenzaldehyde

product: 3‐bromo‐4‐tolualdehyde

product: 3‐chloroacetophenone

product: 3‐chlorobenzaldehyde

product: 2,3,5,6‐tetrachloro‐4‐methylacetophenone
Methanesulfinyl Chloride
Authors: Douglass Irwin B. , Norton Richard V. , Farah Basil Said 
Published: November 2003

Abstract

Methanesulfinyl chloride

reactant: 23.55 g. (0.25 mole) of freshly distilled methyl disulfide

product: methanesulfenyl chloride

byproduct: acetyl chloride

byproduct: methanesulfonyl chloride

byproduct: methyl methanethiolsulfonate
Cholestanyl Methyl Ether
Authors: Neeman M. , Johnson William S. 
Published: November 2003

Abstract

Cholestanyl methyl ether

reactant: 0.200 g. (0.515 mmole) of dry dihydrocholesterol

product: cholestanyl methyl ether

product:
epi
cholestanyl methyl ether

product: cholesteryl methyl ether
Cyclohexyl Isocyanide
Authors: Ugi Ivar , Meyr Rudolf , Lipinski Martin , Bodesheim Ferdinand , Rosendahl Friedrich 
Published: November 2003

Abstract

Cyclohexyl isocyanide

reactant: 127 g. (1.00 mole) of N‐cyclohexylformamide

solvent: 300 ml. of petroleum ether

product: Cyclohexyl isocyanide

product: isopropyl

product:
n
‐butyl

product:
t
‐butyl

product: benzyl
2‐Indanone
Authors: Horan J. E. , Schiessler R. W. 
Published: November 2003

Abstract

2‐Indanone

solvent: 700 ml. of formic acid (88%)

reactant: 116.2 g. (117.3 ml., 1.00 mole) of indene (98%)

product: 2‐indanone
Tetramethylammonium 1,1,2,3,3‐Pentacyanopropenide
Authors: Middleton W. J. , Wiley D. W. 
Published: November 2003

Abstract

Tetramethylammonium 1,1,2,3,3‐pentacyanopropenide

reactant: 6.6 g. (0.10 mole) of malononitrile

product: tetramethylammonium 1,1,2,3,3‐pentacyanopropenide
Diethyl β‐Ketopimelate
Authors: Guha Maya , Nasipuri D. 
Published: November 2003

Abstract

Diethyl β‐ketopimelate

reactant: 89.0 g. (0.5 mole) of γ‐carbethoxybutyryl chloride

intermediate: 50 g. (0.18 mole) of diethyl α‐acetyl‐β‐ketopimelate

product: diethyl β‐ketopimelate
2,4,5,7‐Tetranitrofluorenone
Authors: Newman Melvin S. , Boden H. 
Published: November 2003

Abstract

2,4,5,7‐Tetranitrofluorenone

reactant: 73 g. (0.4 mole) of 9‐fluorenone

product: 2,4,5,7‐tetranitrofluorenone
Diphenylcarbodiimide, MethodI
Authors: Campbell T. W. , Monagle J. J. 
Published: November 2003

AbstractDiphenylcarbodiimide, Method Icatalyst: One gram (0.052 mole) of 3‐methyl‐1‐phenylphospholene 1‐oxideproduct: diphenylcarbodiimide
Ethyl Indole‐2‐Carboxylate
Authors: Noland Wayland E. , Baude Frederic J. 
Published: November 2003

AbstractEthyl indole‐2‐carboxylateproduct: Potassium salt of ethyl o‐nitrophenylpyruvateproduct:Ethyl indole‐2‐carboxylatesolvent: light petroleum ether
Cyclopentanecarboxaldehyde
Authors: Grummitt Oliver , Liska John , Greull Gerhard 
Published: November 2003

Abstract

Cyclopentanecarboxaldehyde

reactant: 740.0 g. (2.49 moles) of reagent mercuric sulfate

reactant: 82.0 g. (101 ml., 1.0 mole) of cyclohexene

product: cyclopentanecarboxaldehyde
3,3‐Pentamethylenediazirine
Authors: Schmitz Ernst , Ohme Roland 
Published: November 2003

Abstract3,3‐Pentamethylenediazirineintermediate:3,3‐Pentamethylenediaziridineproduct:3,3‐Pentamethylenediazirineproduct: 1‐methyl‐3,3‐pentamethylenediaziridineproduct: Cyclohexylhydrazineproduct:n‐propylhydrazineproduct: isopropylhydrazineproduct: benzylhydrazine
2‐Chloro‐1‐formyl‐1‐cyclohexene
Authors: Paquette L. A. , Johnson B. A. , Hinga F. M. 
Published: November 2003

Abstract

2‐Chloro‐1‐formyl‐1‐cyclohexene

product: 2‐Chloro‐1‐formyl‐1‐cyclohexene
1‐(
p
‐Methoxyphenyl)‐5‐Phenyl‐1,3,5‐Pentanetrione
Authors: Miles Marion L. , Harris Thomas M. , Hauser Charles R. 
Published: November 2003

Abstract

1‐(
p
‐Methoxyphenyl)‐5‐phenyl‐1,3,5‐pentanetrione

product: 1‐(
p
‐methoxyphenyl)‐5‐phenyl‐1,3,5‐pentanetrione

reactant: benzoylacetone was obtained from Eastman Kodak (Eastman grade)

product: 1‐phenyl‐1,3,5‐hexanetrione

product: 1,7‐diphenyl‐1,3,5,7‐heptanetetraone

product: 1,5‐diphenyl‐1,3,5‐pentanetrione

product: 1,5‐di(
p
‐methoxyphenyl)‐1,3,5‐pentanetrione
2‐(
p
‐Methoxyphenyl)‐6‐Phenyl‐4‐Pyrone
Authors: Miles Marion L. , Hauser Charles R. 
Published: November 2003

Abstract

2‐(
p
‐methoxyphenyl)‐6‐phenyl‐4‐pyrone

product: 2‐(
p
‐methoxyphenyl)‐6‐phenyl‐4‐pyrone

product: 2‐methyl‐6‐phenyl‐4‐pyrone

product: 2‐(
p
‐chlorophenyl)‐6‐methyl‐4‐pyrone

product: 2,6‐diphenyl‐4‐pyrone

product: 2‐(
p
‐chlorophenyl)‐6‐phenyl‐4‐pyrone

product: 2‐phenyl‐6‐(3‐pyridyl)‐4‐pyrone

product: 5,6,7,8‐tetrahydroflavone

product: 4′‐methoxy‐5,6,7,8‐tetrahydroflavone

product: cyclopenteno[
b
]‐6‐(
p
‐methoxyphenyl)‐4‐pyrone

product: flavone
1‐Methylcyclohexanecarboxylic Acid
Authors: Haaf W. 
Published: November 2003

Abstract

1‐Methylcyclohexanecarboxylic acid

reactant: 28.5 g. (0.25 mole) of 2‐methylcyclohexanol

product: 1‐methylcyclohexanecarboxylic acid

byproduct: 75% cyclohexanecarboxylic acid

product: 2‐Methylbutyric acid

product: Trimethylacetic acid

product: 2,2‐Dimethylbutyric acid

product: Trimethylacetic acid

product: 2,2,3,3‐Tetramethylbutyric acid

product: 2,2‐Dimethylbutyric acid

product: Cyclopentanecarboxylic acid

product: 1‐Methylcyclopentanecarboxylic acid

product: 1‐Methylcyclohexanecarboxylic acid

product:
cis
‐9‐Decalincarboxylic acid

product: 1‐Adamantanecarboxylic acid,H. Stetter, M. Schwarz, and A. Hirschhorn, Ber., 92, 1629 (1959).
Deamination of Amines. 2‐Phenylethyl Benzoate via the Nitrosoamide Decomposition
Authors: White Emil 
Published: November 2003

Abstract

Deamination of Amines. 2‐Phenylethyl Benzoate via the Nitrosoamide Decomposition

intermediate:
N‐(2‐Phenylethyl)benzamide

intermediate:
N‐Nitroso‐N‐(2‐phenylethyl)benzamide

product: 2‐phenylethyl benzoate
2,6‐Dimethyl‐3,5‐Diphenyl‐4
H
‐Pyran‐4‐one
Authors: Emmick Thomas L. , Letsinger Robert L. 
Published: November 2003

Abstract

2,6‐Dimethyl‐3,5‐diphenyl‐4
H
‐pyran‐4‐one

product: 2,6‐dimethyl‐3,5‐diphenyl‐4
H
‐pyran‐4‐one

reactant: Matheson, Coleman and Bell practical grade dibenzyl ketone
Ethyl 2,4‐Diphenylbutanoate
Authors: Kaiser Edwin M. , Kenyon William G. , Hauser Charles R. 
Published: November 2003

Abstract

Ethyl 2,4‐diphenylbutanoate

product: ethyl 2,4‐diphenylbutanoate

product: ethyl 2‐methyl‐2‐phenylpropanoate
2,4‐Nonanedione
Authors: Hampton K. Gerald , Harris Thomas M. , Hauser Charles R. 
Published: November 2003

Abstract

2,4‐Nonanedione

reactant: 60.0 g. (0.600 mole) of 2,4‐pentanedione

product: 2,4‐nonanedione

product: 2,4‐hexanedione

product: 2,4‐tridecanedione
Dimethylketene β‐Lactone Dimer
Authors: Hasek Robert H. , Clark R. Donald , Mayberry Gerald L. 
Published: November 2003

AbstractDimethylketene β‐lactone dimerproduct: β‐lactone dimer of dimethylketenereactant: Tetramethyl‐1,3‐cyclobutanedione is available from Eastman Organic Chemicals
1‐Ethyl‐3‐(3‐Dimethylamino)Propylcarbodiimide Hydrochloride and Methiodide
Authors: Sheehan John C. , Cruickshank Philip A. 
Published: November 2003

Abstract

1‐Ethyl‐3‐(3‐dimethylamino)propylcarbodiimide hydrochloride and methiodide

intermediate: 1‐ethyl‐3‐(3‐dimethylamino)propylcarbodiimide

product:
1‐Ethyl‐3‐(3‐dimethylamino)propylcarbodiimide hydrochloride

product:
1‐Ethyl‐3‐(3‐dimethylamino)propylcarbodiimide methiodide
2,3,4,5,6,6‐Hexamethyl‐2,4‐Cyclohexadien‐1‐one
Authors: Hart Harold , Lange Richard M. , Collins Peter M. 
Published: November 2003

Abstract

2,3,4,5,6,6‐Hexamethyl‐2,4‐cyclohexadien‐1‐one

product: 2,3,4,5,6,6‐hexamethyl‐2,4‐cyclohexadien‐1‐one

product: hexaethyl‐2,4‐cyclohexadienone

product: 3,4,6,6‐tetramethyl‐2,4‐cyclohexadienone
2‐Hydroxy‐3‐methylisocarbostyril
Authors: Moriconi Emil J. , Creegan Francis J. 
Published: November 2003

Abstract

2‐Hydroxy‐3‐methylisocarbostyril

reactant: 8.0 g. (7.5 ml., 0.055 mole) of 2‐methyl‐1‐indanone

product: 2‐hydroxy‐3‐methylisocarbostyril

intermediate: 3‐hydroxy‐2‐methylpropiophenone
1‐Methyl‐3‐
p
‐Tolyltriazene and its Use in the Esterification of Acids
Authors: White E. H. , Baum A. A. , Eitel D. E. 
Published: November 2003

Abstract

1‐Methyl‐3‐
p
‐tolyltriazene and its use in the esterification of acids

product:
1‐Methyl‐3‐p‐tolyltriazene

product: methyl 3,5‐dinitrobenzoate

byproduct: 1,5‐di‐
p
‐tolyl‐3‐methyl‐1,4‐pentazadiene
2‐Phenylperfluoropropene
Authors: Herkes Frank E. , Burton Donald J. 
Published: November 2003

Abstract

2‐Phenylperfluoropropene

solvent: 200 ml. of dry diglyme

product: 2‐phenylperfluoropropene

product: 2‐cyclohexyl‐ (70%)

product: 2‐benzyl‐ (61%)

product: 2‐(
p
‐fluorophenyl)perfluoropropenes (67%)
2‐Bromonaphthalene
Authors: Schaefer J. P. , Higgins Jerry , Shenoy P. K. 
Published: November 2003

Abstract

2‐Bromonaphthalene

product: 2‐bromonaphthalene

solvent: petroleum ether

product: α‐bromonaphthalene

product: 3‐bromopyridine

product: 2‐bromopyridine

product: 8‐bromoquinoline

product:
o
‐bromotoluene

product:
p
‐chlorobromobenzene

product:
p
‐nitrobromobenzene

product:
p
‐methoxybromobenzene
2,7‐Dimethyloxepin
Authors: Paquette L. A. , Barrett J. H. 
Published: November 2003

Abstract

2,7‐Dimethyloxepin

intermediate: 1,2‐dimethyl‐1,4‐cyclohexadiene

intermediate:
1,2‐Dimethyl‐1,2‐epoxycyclohex‐4‐ene

intermediate:
4,5‐Dibromo‐1,2‐dimethyl‐1,2‐epoxycyclohexane

product: 2,7‐dimethyloxepin
Cinnamonitrile
Authors: Lohaus G. 
Published: November 2003

Abstract

Cinnamonitrile

product: cinnamonitrile

product: 2,4‐hexadienenitrile

product: cyclo‐C
6
H
11
CN

product: ClCH
2
CH
2
CN

product: (CH
3
)
3
CCN

product: CH
3
CHCHCHCHCN

product: C
6
H
5
CH
2
CN

product: C
2
H
5
OCOCH
2
CH
2
CN

product: NC‐(CH
2
)
8
CN
Diethyl
trans
‐Δ
4
‐Tetrahydrophthalate
Authors: Sample Thomas E. , Hatch Lewis F. 
Published: November 2003

Abstract

Diethyl
trans
‐Δ
4
‐tetrahydrophthalate

reactant: 60.0 g. (0.508 mole) of 3‐sulfolene

reactant: 86.0 g. (82.0 ml., 0.500 mole) of diethyl fumarate

catalyst: 1.0 g. of hydroquinone

solvent: 200 ml. of petroleum ether

unknown: 4‐
tert
‐Butylcatechol

product: diethyl
trans
‐Δ
4
‐tetrahydrophthalate
N,N
‐Dimethyldodecylamine Oxide
Authors: Sheng M. N. , Zajacek J. G. 
Published: November 2003

Abstract

N,N
‐dimethyldodecylamine oxide

reactant: 21.3 g. (0.100 mole) of freshly distilled
N,N
‐dimethyldodecylamine

product:
N,N
‐dimethyldodecylamine oxide
Ethyl 1‐Naphthylacetate
Authors: Lee Ving , Newman Melvin S. 
Published: November 2003

Abstract

Ethyl 1‐Naphthylacetate

reactant: 30.5 g. (0.160 mole) of 1‐naphthoyl chloride

intermediate: 1‐(diazoacetyl)naphthalene

product: ethyl 1‐naphthylacetate

reactant: 1‐naphthoic acid

reactant: 1‐bromonaphthalene

solvent: propyl 1‐naphthylacetate
Δ9,10‐Octalin
Authors: Kaiser Edwin M. , Benkeser Robert A. 
Published: November 2003

AbstractΔ9,10‐octalinsolvent: 250 ml. of anhydrous ethylamineproduct: Δ9,10‐octalinbyproduct: Δ1,9‐octalinproduct: dimethylamineproduct: 1‐tert‐butylcyclohexene
1‐Phenyl‐1,4‐Pentadiyne and 1‐Phenyl‐1,3‐Pentadiyne
Authors: Taniguchi H. , Mathai I. M. , Miller Sidney I. 
Published: November 2003

Abstract

1‐Phenyl‐1,4‐pentadiyne and 1‐phenyl‐1,3‐pentadiyne

reactant: 102 g. (1.00 mole) of phenylacetylene

reactant: 96 g. (0.81 mole) of propargyl bromide

product: 1‐phenyl‐1,4‐pentadiyne

product: 1‐phenyl‐1,3‐pentadiyne
Aldehydes from Allylic Alcohols and Phenylpalladium Acetate: 2‐Methyl‐3‐Phenylpropionaldehyde
Authors: Heck R. F. 
Published: November 2003

Abstract

Aldehydes from allylic alcohols and Phenylpalladium acetate: 2‐Methyl‐3‐phenylpropionaldehyde

product: 2‐methyl‐3‐phenylpropionaldehyde

product: cinnamaldehyde

product: C
6
H
5
CH
2
CH
2
CHO

product: C
6
H
5
CH(CH
3
)CH
2
CHO

product: C
6
H
5
CH(CH
3
)CH
2
COCH
3

product: C
6
H
5
C(CH
3
)
2
CH
2
COCH
3
1‐
d
‐Aldehydes from Organometallic Reagents: 2‐Methylbutanal‐1‐
d
Authors: Niznik G. E. , Morrison W. H. , Walborsky H. M. 
Published: November 2003

Abstract

1‐
d
‐Aldehydes from organometallic reagents: 2‐methylbutanal‐1‐
d

reactant: 118 g. (0.752 mole) of
N
‐(1,1,3,3‐tetramethylbutyl)formamide

solvent: 1500 ml. of
N,N
‐dimethylformamide

intermediate: 1,1,3,3‐tetramethylbutyl isonitrile

intermediate: N‐(2‐
Methylbutylidene
‐1‐
d
)‐1,1,3,3‐
tetramethylbutylamine

product: 2‐methylbutanal‐1‐
d
,
Aldehydes from sym‐Trithiane: n‐Pentadecanal
Authors: Seebach D. , Beck A. K. 
Published: November 2003

Abstract

Aldehydes from
sym
‐Trithiane:
n
‐Pentadecanal

reactant: 25.0 g. (0.180 mole) of finely ground, pure,
sym
‐trithiane

intermediate: 2‐tetradecyl‐
sym
‐trithiane

intermediate: acetal

product:
n
‐pentadecanal

product: Hexanal

product: (S)‐(−)‐3‐Methylpentanal

product: Octanal

product: Undecanal

product: Heptadecanal

product: Phenylacetaldehyde
Alkyl Iodides: Neopentyl Iodide and Iodocyclohexane
Authors: Rydon H. N. 
Published: November 2003

Abstract

Alkyl iodides: neopentyl iodide and iodocyclohexane

product: neopentyl iodide

product: iodocyclohexane

product:
n
‐Butyl iodide

product:
n
‐Hexyl iodide

product: 2‐Phenylethyl iodide

product: 1,3‐Diiodo‐2,2‐dimethylpropanea

product:
tert
‐Amyl iodide

product: Ethyl 3‐iodopropionate
2‐Bornene
Authors: Shapiro Robert H. , Duncan J. H. 
Published: November 2003

Abstract

2‐Bornene

reactant: 32 g. (0.10 mole) of camphor tosylhydrazone

product: 2‐bornene

product: 3‐methylcyclohexene

product: cholest‐6‐ene

product: androst‐16‐ene

product: allylbenzene

byproduct: isobutylbenzene
Cyclic Ketones from 1,3‐Dithiane: Cyclobutanone
Authors: Seebach D. , Beck A. K. 
Published: November 2003

Abstract

Cyclic ketones from 1,3‐dithiane: cyclobutanone

reactant: 65.5 g. (44.5 ml., 0.417 mole) of 1‐bromo‐3‐chloropropane

intermediate: 5,9‐dithiaspiro[3.5]nonane

product: cyclobutanone
Methyl (
trans
‐2‐Iodo‐1‐Tetralin)Carbamate
Authors: Heathcock C. H. , Hassner A. 
Published: November 2003

Abstract

Methyl (
trans
‐2‐Iodo‐1‐Tetralin)Carbamate

product: methyl (
trans
‐2‐iodo‐1‐tetralin)carbamate
Controlled‐Potential Electrolytic Reduction: 1,1‐Bis(bromomethyl)cyclopropane
Authors: Rifi M. R. 
Published: November 2003

Abstract

Controlled‐potential electrolytic reduction: 1,1‐bis(bromomethyl)cyclopropane

reactant: 1.5 M tetraethylammonium tetrafluoroborate

solvent:
N,N
‐dimethylformamide

reactant: 25.0 g. (0.0651 mole) of pentaerythrityl tetrabromide

solvent: 250 ml. of 0.2 M tetra‐
n
‐butylammonium bromide

product: 1,1‐bis‐(bromomethyl)cyclopropane

product: spiropentane

product: CH
3
(CH
2
)
3
CH
3
1,2‐Diaroylcyclopropanes:
trans
‐1,2‐Dibenzoylcyclopropane
Authors: Colon Ismael , Griffin Gary W. , O'Connell E. J. 
Published: November 2003

Abstract

1,2‐Diaroylcyclopropanes:
trans
‐1,2‐Dibenzoylcyclopropane

product:
trans
‐1,2‐dibenzoylcyclopropane
Preparation of Cyano Compounds Using Alkylaluminum Intermediates: 1‐Cyano‐6‐Methoxy‐3,4‐Dihydronaphthalene
Authors: Nagata W. , Yoshioka M. , Murakami M. 
Published: November 2003

Abstract

Preparation of cyano compounds using alkylaluminum intermediates: 1‐cyano‐6‐methoxy‐3,4‐dihydronaphthalene

reactant: 6.15 g. (0.0347 mole) of 6‐methoxy‐1‐tetralone

intermediate:
p
‐toluenesulfonic acid monohydrate

solvent: 1 l. of 40% ether in petroleum ether

product: 1‐cyano‐6‐methoxy‐3,4‐dihydronaphthalene
2,2,3,3‐Tetramethyliodocyclopropane
Authors: Marolewski T. A. , Yang N. C. 
Published: November 2003

Abstract

2,2,3,3‐Tetramethyliodocyclopropane

product: 1‐Iodo‐
cis,trans
‐2,3‐dimethylcyclopropane

product: 2,2,3,3‐tetramethyliodocyclopropane
2‐
tert
‐Butyl‐1,3‐diaminopropane
Authors: Hutchins R. O. , Maryanoff B. E. 
Published: November 2003

Abstract

2‐
tert
‐butyl‐1,3‐diaminopropane

reactant: 45.0 g. (0.682 mole) of malononitrile

product: 2‐tert‐
Butyl
‐1,3‐
diaminopropane.

intermediate:
tert
‐butylmalononitrile (30.5 g., 0.250 mole)

reactant: boron trifluoride diethyl etherate (85.3 g., 0.600 mole)
Diamantane: Pentacyclo[7.3.1.1
4,12
.0
2,7
.0
6,11
]tetradecane
Authors: Gund Tamara M. , Thielecke Wilfried , Schleyer Paul v. R. 
Published: November 2003

Abstract

Diamantane: Pentacyclo[7.3.1.1
4,12
.0
2,7
.0
6,11
]tetradecane

intermediate: Binor‐S

intermediate: tetrahydro‐Binor‐S

product: diamantane
Diethyl 2‐(Cyclohexylamino)Vinylphosphonate
Authors: Nagata Wataru , Wakabayashi Toshio , Hayase Yoshio 
Published: November 2003

Abstract

Diethyl 2‐(cyclohexylamino)vinylphosphonate

reactant: 410 g. (2.08 moles) of bromoacetaldehyde diethyl acetal

reactant: 316 g. (1.90 moles) of triethyl phosphite

intermediate: 192 g. (0.755 mole) of diethyl 2,2‐diethoxyethylphosphonate

intermediate: 90.0 g. (0.500 mole) of diethyl formylmethylphosphonate

product: diethyl 2‐(cyclohexylamino)vinylphosphonate
Directed Lithiation of Aromatic Compounds: (2‐Dimethylamino‐5‐Methylphenyl)Diphenylcarbinol
Authors: Hay J. V. , Harris T. M. 
Published: November 2003

Abstract

Directed lithiation of aromatic compounds: (2‐dimethylamino‐5‐methylphenyl)diphenylcarbinol

product: (2‐dimethylamino‐5‐methylphenyl)diphenylcarbinol

catalyst: 8.8 g. (0.076 mole of
N,N,N′,N′
‐tetramethylethylenediamine
Ketones and Alcohols from Organoboranes: Phenyl Heptyl Ketone, 1‐Hexanol, and 1‐Octanol
Authors: Kono Hiromichi , Hooz John 
Published: November 2003

Abstract

Ketones and alcohols from organoboranes: phenyl heptyl ketone, 1‐hexanol, and 1‐octanol

product: phenyl heptyl ketone

product: 1‐hexanol

reactant: 11.2 g. (0.100 mole) of 1‐octene

byproduct: 3‐methyl‐2‐butanol

product: 1‐octanol
Orcinol Monomethyl Ether
Authors: Mirrington R. N. , Feutrill G. I. 
Published: November 2003

Abstract

Orcinol Monomethyl Ether

intermediate: orcinol dimethyl ether

solvent: 250 ml. of dry
N,N
‐dimethylformamide

reactant: 31 g. (37 ml., 0.50 mole) of ethanethiol

solvent: 250‐ml. portions of petroleum ether

product: orcinol monomethyl ether
1‐Phenyl‐4‐Phosphorinanone
Authors: Snider Theodore E. , Morris Don L. , Srivastava K. C. , Berlin K. D. 
Published: November 2003

Abstract

1‐Phenyl‐4‐phosphorinanone

intermediate: bis(2‐cyanoethyl)phenylphosphine

intermediate: 4‐amino‐1,2,5,6‐tetrahydro‐1‐phenylphosphorin‐3‐carbonitrile

product: 1‐phenyl‐4‐phosphorinanone

intermediate: hydrochloride salt of 1‐phenyl‐4‐phosphorinanone
Preparation of α,β‐Unsaturated Aldehydes
via
the
W
ittig Reaction: Cyclohexylideneacetaldehyde
Authors: Nagata Wataru , Wakabayashi Toshio , Hayase Yoshio 
Published: November 2003

Abstract

Preparation of α,β‐unsaturated aldehydes
via
the wittig reaction: cyclohexylideneacetaldehyde

product: cyclohexylideneacetaldehyde

byproduct: cyclohexenylacetaldehyde
Selective α‐Bromination of an Aralkyl Ketone with Phenyltrimethylammonium Tribromide: 2‐Bromoacetyl‐6‐Methoxynaphthalene and 2,2‐Dibromoacetyl‐6‐Methoxynaphthalene
Authors: Jacques J. , Marquet A. 
Published: November 2003

Abstract

Selective α‐bromination of an aralkyl ketone with phenyltrimethylammonium tribromide: 2‐bromoacetyl‐6‐methoxynaphthalene and 2,2‐dibromoacetyl‐6‐methoxynaphthalene

reactant: 24.8 g. (25.9 ml., 0.205 mole) of freshly distilled
N,N
‐dimethylaniline

reactant: 25 g. (19 ml., 0.20 mole) of distilled dimethyl sulfate

intermediate: phenyltrimethylammonium sulfomethylate

reactant: phenyltrimethylammonium tribromide (PTT)

product: 2‐bromoacetyl‐6‐methoxynaphthalene

product: 2,2‐dibromoacetyl‐6‐methoxynaphthalene
Stereoselective Synthesis of Trisubstituted Olefins: Ethyl 4‐Methyl‐(
E
)‐4,8‐Nonadienoate
Authors: Trust Ronald I. , Ireland Robert E. 
Published: November 2003

Abstract

Stereoselective synthesis of trisubstituted olefins: ethyl 4‐methyl‐(
E
)‐4,8‐nonadienoate

reactant: 49.4 g. (0.546 mole) of 4‐chloro‐1‐butene

reactant: 40.1 g. (0.572 mole) of methacrolein

intermediate: 2‐methyl‐1,6‐heptadien‐3‐ol

reactant: 186 g. (1.15 moles) of ethyl orthoacetate

reactant: 0.70 g. (0.0094 mole) of propionic acid

product: ethyl 4‐methyl‐(
E
)‐4,8‐nonadienoate

reactant: 3‐buten‐1‐ol
[18]Annulene
Authors: Stöckel K. , Sondheimer F. 
Published: November 2003

Abstract

[18]annulene

intermediate:
Hexadehydro
[18]
annulene

intermediate:
Tridehydro
[18]
annulene

reactant: 1,5‐Hexadiyne was obtained from Farchan Research Laboratories

solvent: “pentane” petroleum spirit (b.p. 25–40°) available from Hopkin & Williams Ltd., Hadwell Heath, England

product: [18]annulene
Trimethylene Dithiotosylate and Ethylene Dithiotosylate
Authors: Woodward R. B. , Pachter I. J. , Scheinbaum Monte L. 
Published: November 2003

Abstract

Trimethylene dithiotosylate and ethylene dithiotosylate

intermediate:
Potassium thiotosylate

product:
Trimethylene dithiotosylate

product:
Ethylene dithiotosylate

reactant:
p
‐toluenesulfonyl chloride

reactant: Trimethylene dibromide, available from Eastman Organic Chemicals

byproduct: tosyltrimethylene thiotosylate, CH
3
C
6
H
4
SO
2
(CH
2
)
3
SSO
2
C
6
H
4
CH
3
5β‐Cholest‐3‐ene‐5‐Acetaldehyde
Authors: Ireland R. E. , Dawson D. J. 
Published: November 2003

Abstract

5β‐cholest‐3‐ene‐5‐acetaldehyde

reactant: 970 mg. (2.51 mmoles) of cholest‐4‐en‐3β‐ol

reactant: Ethyl vinyl ether

solvent: 150 ml. of petroleum ether

intermediate: cholestenyl vinyl ether

product: 5β‐cholest‐3‐ene‐5‐acetaldehyde
Ethyl 5β‐Cholest‐3‐ene‐5‐Acetate
Authors: Ireland R. E. , Dawson D. J. 
Published: November 2003

Abstract

Ethyl 5β‐cholest‐3‐ene‐5‐acetate

reactant: 970 mg. (2.50 mmoles) of cholest‐4‐en‐3β‐ol

reactant: Triethyl orthoacetate

product: ethyl 5β‐cholest‐3‐ene‐5‐acetate

solvent: Baker petroleum ether
N,N
‐Dimethyl‐5β‐Cholest‐3‐ene‐5‐Acetamide
Authors: Ireland R. E. , Dawson D. J. 
Published: November 2003

Abstract

N,N
‐dimethyl‐5β‐cholest‐3‐ene‐5‐acetamide

reactant: 970 mg. (2.51 mmoles) of cholest‐4‐en‐3β‐ol

product:
N,N
‐dimethyl‐5β‐cholest‐3‐ene‐5‐acetamide
Endocyclic Enamine Synthesis:
N
‐Methyl‐2‐Phenyl‐Δ
2
‐Tetrahydropyridine
Authors: Evans D. A. , Domeier L. A. 
Published: November 2003

Abstract

Endocyclic enamine synthesis:
N
‐methyl‐2‐phenyl‐Δ
2
‐tetrahydropyridine

intermediate: N‐(α‐
Methylbenzylidene
)
methylamine

intermediate: N‐
Methyl
‐2‐
phenyl
‐Δ
2
‐
tetrahydropyridine
para
‐Bromination of Aromatic Amines: 4‐Bromo‐
N,N
‐dimethyl‐3‐(trifluoromethyl)aniline
Authors: Fox G. J. , Hallas G. , Hepworth J. D. , Paskins K. N. 
Published: November 2003

Abstract

para
‐Bromination of aromatic amines: 4‐bromo‐
N,N
‐dimethyl‐3‐(trifluoromethyl)aniline

reactant: 66.2 g. (0.200 mole) of 2,4,6‐tribromophenol

intermediate: 20.5 g. (0.0500 mole) of finely powdered 2,4,4,6‐tetrabromo‐2,5‐cyclohexadien‐1‐one

product: 4‐bromo‐
N,N
‐dimethyl‐3‐(trifluoromethyl)aniline

solvent: petroleum ether

product: 2‐amino‐5‐bromopyrimidine

product: 2‐amino‐5‐bromobenzoic acid