bluuebunny/crossref_metadata_2025 huggingface dataset:
3‐Benzyl‐3‐Methylpentanoic Acid
Authors: Prout F. S. , Hartman R. J. , Huang E. P.‐Y. , Korpics C. J. , Tichelaar G. R.
Published: November 2003

3‐Benzyl‐3‐methylpentanoic acid

reactant: 113 g. (106 ml., 1.0 mole) of ethyl cyanoacetate

intermediate: ethyl
sec
‐butylidenecyanoacetate

intermediate: 155 g. (0.6 mole) of ethyl 3‐benzyl‐2‐cyano‐3‐methylpentanoate

intermediate: 93.6 g. (0.5 mole) of 3‐benzyl‐3‐methylpentanenitrile

byproduct: bibenzyl

byproduct: ethyl
sec
‐butylcyanoacetate

product: 3‐benzyl‐3‐methylpentanoic acid

byproduct: 3‐ethyl‐3‐methylhexanoic acid
N‐Chlorobetainyl Chloride
Authors: Vassel B. , Skelly W. G.
Published: November 2003

N‐chlorobetainyl chloride

product: N‐chlorobetainyl chloride is 337–344 g. (98–100%) of 98–100%
1‐(
p
‐Chlorophenyl)‐3‐Phenyl‐2‐Propanone
Authors: Coan Stephen B. , Becker Ernest I.
Published: November 2003

1‐(
p
‐Chlorophenyl)‐3‐Phenyl‐2‐Propanone

product: 1‐(
p
‐chlorophenyl)‐3‐phenyl‐2‐propanone

solvent: 160 ml. of petroleum ether
Cholesterol, Δ5‐Cholesten‐3‐One, and Δ4‐Cholesten‐3‐One
Authors: Fieser Louis F.
Published: November 2003

Cholesterol,* Δ5‐cholesten‐3‐one,* and Δ4‐cholesten‐3‐one

intermediate:Cholesterol dibromide

product: cholesterol

product:5α,6β‐Dibromocholestan‐3‐one

product: Δ5‐Cholesten‐3‐one

product: Δ4‐Cholesten‐3‐one
Diacetyl‐
d
‐tartaric Anhydride
Authors: Shriner R. L. , Furrow C. L.
Published: November 2003

Diacetyl‐
d
‐tartaric anhydride

product: diacetyl‐
d
‐tartaric anhydride
Diethyl Mercaptoacetal
Authors: Parham William E. , Wynberg Hans
Published: November 2003

Diethyl mercaptoacetal

reactant: 588 g. (3 moles) of diethyl bromoacetal

intermediate: 500 g. (1.38 moles, calculated as tetrasulfide) of 1,1,1′,1′‐tetraethoxyethyl polysulfide

byproduct: 1,1,1′,1′‐tetraethoxyethyl sulfide

product: Diethyl mercaptoacetal
Diethylthiocarbamyl Chloride
Authors: Goshorn R. H. , Levis W. W. , Jaul E. , Ritter E. J.
Published: November 2003

Diethylthiocarbamyl chloride

byproduct: sulfur

product: diethylthiocarbamyl chloride

product: dimethylthiocarbamyl chloride

product: diisopropylthiocarbamyl chloride

product: diisobutylthiocarbamyl chloride
Thiobenzophenone
Authors: Gofton B. F. , Braude E. A.
Published: November 2003

Thiobenzophenone

product: thiobenzophenone

solvent: 20 ml. of petroleum ether
α‐Chlorophenylacetic Acid
Authors: Eliel Ernest L. , Fisk Milton T. , Prosser Thomas
Published: November 2003

α‐Chlorophenylacetic acid

intermediate: ethyl mandelate

intermediate: ethyl α‐chlorophenylacetate

product: α‐
Chlorophenylacetic acid
1‐Cyano‐3‐Phenylurea
Authors: Kurzer Frederick , Powell J. Roy
Published: November 2003

1‐Cyano‐3‐phenylurea

product: 1‐cyano‐3‐phenylurea

solvent: 30–40 ml. of petroleum ether (boiling range 40–60°)

product: 1‐cyano‐3‐α‐naphthylurea
1,2‐Cyclodecanediol
Authors: Blomquist A. T. , Goldstein Albert
Published: November 2003

1,2‐Cyclodecanediol

product:
cis
‐1,2‐cyclodecanediol

product:
trans
‐1,2‐cyclodecanediol
N,N′‐Diethylbenzidine
Authors: Rice Rip G. , Kohn Earl J.
Published: November 2003

N,N′‐diethylbenzidine

product: N,N′‐dibutylbenzidine

product: N‐hexylaniline

product: N‐Propylbutylamine

product: N,N′‐Diethylbenzidine
Laurylmethylamine
Authors: Wilson C. V. , Stenberg J. F.
Published: November 2003

Laurylmethylamine

reactant: 160 g. (0.75 mole) of N‐methyllauramide

product: laurylmethylamine
p‐Methoxyphenylacetonitrile
Authors: Rorig Kurt , Johnston J. Derland , Hamilton Robert W. , Telinski Thomas J.
Published: November 2003

p‐Methoxyphenylacetonitrile

product:p‐methoxyphenylacetonitrile

product:p‐chlorophenylacetonitrile
α‐Naphthyl Isothiocyanate
Authors: Cymerman‐Craig J. , Moyle M. , White R. A.
Published: November 2003

α‐Naphthyl isothiocyanate

reactant: 16.2 g. (0.08 mole) of dry α‐naphthylthiourea

product: α‐naphthyl isothiocyanate

product: phenyl

product:
o
‐chlorophenyl

product:
p
‐bromophenyl

product:
p
‐biphenylyl

product: β‐naphthyl

product: 9‐phenanthryl

product: 1‐pyrenyl
Sebacil
Authors: Blomquist A. T. , Goldstein Albert
Published: November 2003

Sebacil

product: sebacil
2,4,6‐Tribromobenzoic Acid
Authors: Robison Michael M. , Robison Bonnie L.
Published: November 2003

2,4,6‐Tribromobenzoic acid

intermediate:
3‐Amino‐2,4,6‐tribromobenzoic acid.

product: 2,4,6‐tribromobenzoic acid
2‐Chloro‐2‐Methylcyclohexanone and 2‐Methyl‐2‐Cyclohexenone
Authors: Warnhoff E. W. , Martin D. G. , Johnson William S.
Published: November 2003

2‐Chloro‐2‐methylcyclohexanone and 2‐methyl‐2‐cyclohexenone

product: 2‐methyl‐2‐cyclohexenone

product: 2‐chloro‐2‐methylcyclohexanone

byproduct: 2‐methylenecyclohexanone
1,4‐Diphenyl‐5‐Amino‐1,2,3‐Triazole and 4‐Phenyl‐5‐Anilino‐1,2,3‐Triazole
Authors: Lieber Eugene , Chao Tai Siang , Rao C. N. Ramachandra
Published: November 2003

1,4‐Diphenyl‐5‐amino‐1,2,3‐triazole and 4‐phenyl‐5‐anilino‐1,2,3‐triazole

reactant: 35.7 g. (0.3 mole) of phenyl azide

product: Six grams (0.025 mole) of 1,4‐diphenyl‐5‐amino‐1,2,3‐triazole

product: 4‐phenyl‐5‐anilino‐1,2,3‐triazole
2‐Benzylaminopyridine
Authors: Sprinzak Yaïr
Published: November 2003

2‐Benzylaminopyridine

product: 2‐benzylaminopyridine

product: N,N′‐dibenzyl‐
p
‐phenylenediamine

product: N‐Benzylaniline
2‐Bromo‐3‐Methylbenzoic Acid
Authors: Bunnett J. F. , Rauhut M. M.
Published: November 2003

2‐bromo‐3‐methylbenzoic acid

intermediate: 2‐bromo‐4‐nitrotoluene

solvent: 500 ml. of petroleum ether

product: 2‐bromo‐3‐methylbenzoic acid
Dibromoacetonitrile
Authors: Wilt James W. , Diebold James L.
Published: November 2003

Dibromoacetonitrile

reactant: 63.8 g. (0.75 mole) of cyanoacetic acid

product: dibromoacetonitrile

product: Dichloroacetonitrile
5‐Formyl‐4‐Phenanthroic Acid
Authors: Dessy R. E. , Newman M. S.
Published: November 2003

5‐Formyl‐4‐phenanthroic acid

product: 5‐formyl‐4‐phenanthroic acid
1‐Methylisoquinoline
Authors: Weinstock J. , Boekelheide V.
Published: November 2003

1‐Methylisoquinoline

intermediate: 1‐cyano‐2‐benzoyl‐1,2‐dihydroisoquinoline

intermediate: 2‐benzoyl‐1‐cyano‐1‐methyl‐1,2‐dihydroisoquinoline

product: 1‐methylisoquinoline
1,4‐Pentadiene
Authors: Benson R. E. , McKusick B. C. , Grummitt Oliver , Budewitz E. P. , Chudd C. C.
Published: November 2003

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
α‐Phthalimido‐
o
‐toluic Acid
Authors: Bornstein J. , Drummond P. E. , Bedell S. F.
Published: November 2003

α‐Phthalimido‐
o
‐toluic acid

product: α‐phthalimido‐
o
‐toluic acid
trans
‐Stilbene Oxide
Authors: Reif Donald J. , House Herbert O.
Published: November 2003

trans
‐Stilbene Oxide

product:
trans
‐stilbene oxide
Di‐
n
‐butyldivinyltin
Authors: Seyferth Dietmar
Published: November 2003

Di‐
n
‐butyldivinyltin

product: di‐
n
‐butyldivinyltin
Dicyanoketene Ethylene Acetal
Authors: Dickinson C. L. , Melby L. R.
Published: November 2003

Dicyanoketene ethylene acetal

product: dicyanoketene ethylene acetal
9,10‐Dihydroxystearic Acid
Authors: Swern Daniel , Scanlan John T. , Dickel Geraldine B.
Published: November 2003

9,10‐Dihydroxystearic Acid

solvent: 425 ml. of formic acid

product: 9,10‐dihydroxystearic acid
N,N‐Dimethylcyclohexylmethylamine
Authors: Cope Arthur C. , Ciganek Engelbert
Published: November 2003

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

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.
Methyl Cyclopentanecarboxylate
Authors: Goheen D. W. , Vaughan W. R.
Published: November 2003

Methyl Cyclopentanecarboxylate

product: methyl cyclopentanecarboxylate

reactant: 2‐chlorocyclohexanone
3‐Methyl‐2‐Furoic Acid and 3‐Methylfuran
Authors: Burness D. M.
Published: November 2003

3‐Methyl‐2‐furoic acid and 3‐methylfuran

product: 3‐methyl‐2‐furoic acid

product: 3‐methylfuran
Triptycene
Authors: Wittig George
Published: November 2003

Triptycene

product: triptycene
3‐Bromoacetophenone
Authors: Pearson D. E. , Pope H. W. , Hargrove W. W.
Published: November 2003

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
2,5‐Dihydro‐2,5‐dimethoxyfuran
Authors: Burness D. M.
Published: November 2003

2,5‐Dihydro‐2,5‐dimethoxyfuran

product: 2,5‐Dihydro‐2,5‐dimethoxyfuran
Methanesulfinyl Chloride
Authors: Douglass Irwin B. , Norton Richard V. , Farah Basil Said
Published: November 2003

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

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

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

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

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

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
9,10‐Dihydroanthracene
Authors: Bass K. C.
Published: November 2003

9,10‐dihydroanthracene

product: 9,10‐dihydroanthracene

byproduct: anthracene
Dimesitylmethane
Authors: Cornell John H. , Gollis Morton H.
Published: November 2003

Dimesitylmethane

product: dimesitylmethane
Hexahydroxybenzene
Authors: Fatiadi A. J. , Sager W. F.
Published: November 2003

Hexahydroxybenzene

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

2,4,5,7‐Tetranitrofluorenone

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

product: 2,4,5,7‐tetranitrofluorenone
Tetrolic Acid
Authors: Kauer J. C. , Brown M.
Published: November 2003

Tetrolic Acid

product: tetrolic acid

product: phenylpropiolic acid
1‐Bromo‐2‐Fluorobenzene
Authors: Rutherford K. G. , Redmond W.
Published: November 2003

1‐Bromo‐2‐fluorobenzene

intermediate:
o
‐bromobenzenediazonium hexafluorophosphate

product: 1‐bromo‐2‐fluorobenzene
Diphenylcarbodiimide, MethodI
Authors: Campbell T. W. , Monagle J. J.
Published: November 2003

Diphenylcarbodiimide, Method I

catalyst: One gram (0.052 mole) of 3‐methyl‐1‐phenylphospholene 1‐oxide

product: diphenylcarbodiimide
Ethyl Indole‐2‐Carboxylate
Authors: Noland Wayland E. , Baude Frederic J.
Published: November 2003

Ethyl indole‐2‐carboxylate

product: Potassium salt of ethyl o‐nitrophenylpyruvate

product:Ethyl indole‐2‐carboxylate

solvent: light petroleum ether
Indole‐3‐carbonitrile
Authors: Blatter H. M. , Lukaszewski H. , de Stevens G.
Published: November 2003

Indole‐3‐carbonitrile

product: indole‐3‐carbonitrile
2,3‐Naphthalenedicarboxylic Acid
Authors: Friedman Lester
Published: November 2003

2,3‐Naphthalenedicarboxylic acid

product: 2,3‐naphthalenedicarboxylic acid

product: 2‐naphthoic acid
1‐Adamantanecarboxylic Acid
Authors: Koch H. , Haaf W.
Published: November 2003

1‐Adamantanecarboxylic acid

product: 1‐adamantanecarboxylic acid

intermediate: Methyl 1‐adamantanecarboxylate
Cyclopentanecarboxaldehyde
Authors: Grummitt Oliver , Liska John , Greull Gerhard
Published: November 2003

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
N‐Ethylallenimine
Authors: Bottini Albert T. , Olsen Robert E.
Published: November 2003

N‐ethylallenimine

product: N‐ethylallenimine

byproduct: N‐ethylpropargylamine
Homophthalic Acid
Authors: Smith P. A. S. , Kan R. O.
Published: November 2003

Homophthalic Acid

product: homophthalic acid
α‐Ketoglutaric Acid
Authors: Bottorff E. M. , Moore L. L.
Published: November 2003

α‐Ketoglutaric acid

intermediate:
Triethyl oxalylsuccinate

product: α‐
Ketoglutaric acid
2,4,6‐Trimethylpyrylium Perchlorate
Authors: Balaban A. T. , Nenitzescu C. D. , Hafner K. , Kaiser H.
Published: November 2003

2,4,6‐Trimethylpyrylium perchlorate

product: 2,4,6‐trimethylpyrylium perchlorate
Aminoacetone Semicarbazone Hydrochloride
Authors: Hepworth John D.
Published: November 2003

Aminoacetone semicarbazone hydrochloride

intermediate: 52 g. (0.45 mole) of the acetamidoacetone

intermediate: Aminoacetone hydrochloride

product: aminoacetone semicarbazone hydrochloride
D,L
‐Ketopinic Acid
Authors: Bartlett Paul D. , Knox L. H.
Published: November 2003

D,L
‐ketopinic acid

product:
D,L
‐Ketopinic acid
3,3‐Pentamethylenediazirine
Authors: Schmitz Ernst , Ohme Roland
Published: November 2003

3,3‐Pentamethylenediazirine

intermediate:3,3‐Pentamethylenediaziridine

product:3,3‐Pentamethylenediazirine

product: 1‐methyl‐3,3‐pentamethylenediaziridine

product: Cyclohexylhydrazine

product:n‐propylhydrazine

product: isopropylhydrazine

product: benzylhydrazine
9‐Phenylphenanthrene
Authors: Mallory Frank B. , Wood Clelia S.
Published: November 2003

9‐Phenylphenanthrene

reactant: 2.56 g. (0.01 mole) of triphenylethylene

product: 9‐phenylphenanthrene
3‐Phenylsydnone
Authors: Thoman Charles J. , Voaden Denys J.
Published: November 2003

3‐Phenylsydnone

intermediate: 99 g. (0.55 mole) of N‐nitroso‐N‐phenylglycine

product: 3‐phenylsydnone
1‐Bromo‐2‐Fluoroheptane
Authors: Dean F. H. , Amin J. H. , Pattison F. L. M.
Published: November 2003

1‐Bromo‐2‐fluoroheptane

product: 1‐bromo‐2‐fluoroheptane
2‐Chloro‐1‐formyl‐1‐cyclohexene
Authors: Paquette L. A. , Johnson B. A. , Hinga F. M.
Published: November 2003

2‐Chloro‐1‐formyl‐1‐cyclohexene

product: 2‐Chloro‐1‐formyl‐1‐cyclohexene
Hexamethylphosphorous Triamide
Authors: Mark V.
Published: November 2003

Hexamethylphosphorous Triamide

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

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

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

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).
Bis(1,3‐Diphenylimidazolidinylidene‐2)
Authors: Wanzlick H.‐W.
Published: November 2003

Bis(1,3‐diphenylimidazolidinylidene‐2)

product: bis(1,3‐diphenylimidazolidinylidene‐2)
Deamination of Amines. 2‐Phenylethyl Benzoate via the Nitrosoamide Decomposition
Authors: White Emil
Published: November 2003

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
6‐(Dimethylamino)fulvene
Authors: Hafner K. , Vöpel K. H. , Ploss G. , König C.
Published: November 2003

6‐(Dimethylamino)fulvene

solvent: 1.5 l. of petroleum ether

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

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

Ethyl 2,4‐diphenylbutanoate

product: ethyl 2,4‐diphenylbutanoate

product: ethyl 2‐methyl‐2‐phenylpropanoate
Ketene Di(2‐Methoxyethyl) Acetal
Authors: Kuryla William C. , Hyre John E.
Published: November 2003

Ketene di(2‐methoxyethyl) acetal

product: ketene di(2‐methoxyethyl) acetal
2,4‐Nonanedione
Authors: Hampton K. Gerald , Harris Thomas M. , Hauser Charles R.
Published: November 2003

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
Octanal
Authors: Franzen Volker
Published: November 2003

Octanal

reactant: 30 g. (0.4 mole) of anhydrous trimethylamine oxide

product: octanal
Cyclodecanone
Authors: Burpitt R. D. , Thweatt J. G.
Published: November 2003

Cyclodecanone

intermediate: N‐(1‐cycloocten‐1‐yl)pyrrolidine

product: cyclodecanone
Diaminomaleonitrile (Hydrogen Cyanide Tetramer)
Authors: Ferris J. P. , Sanchez R. A.
Published: November 2003

Diaminomaleonitrile (Hydrogen Cyanide Tetramer)

product: Hydrogen cyanide tetramer
Dimethylketene β‐Lactone Dimer
Authors: Hasek Robert H. , Clark R. Donald , Mayberry Gerald L.
Published: November 2003

Dimethylketene β‐lactone dimer

product: β‐lactone dimer of dimethylketene

reactant: 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

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

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

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

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

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%)
Vinyl Triphenylphosphonium Bromide
Authors: Schweizer Edward E. , Bach Robert D.
Published: November 2003

Vinyl triphenylphosphonium bromide

solvent: 1 lb. of reagent grade phenol

product: vinyl triphenylphosphonium bromide
2‐Bromonaphthalene
Authors: Schaefer J. P. , Higgins Jerry , Shenoy P. K.
Published: November 2003

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
t
‐Butyl Hypochlorite
Authors: Mintz M. J. , Walling C.
Published: November 2003

t
‐Butyl hypochlorite

product:
t
‐butyl hypochlorite
2,6‐Dichloronitrobenzene
Authors: Pagano A. S. , Emmons W. D.
Published: November 2003

2,6‐Dichloronitrobenzene

product: 2,6‐dichloronitrobenzene
3,3′‐Dihydroxybiphenyl
Authors: McOmie J. F. W. , West D. E.
Published: November 2003

3,3′‐Dihydroxybiphenyl

solvent: 120 ml. of methylene chloride

product: 3,3′‐dihydroxybiphenyl
2,7‐Dimethyloxepin
Authors: Paquette L. A. , Barrett J. H.
Published: November 2003

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

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

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
trans
‐1,2‐Dihydrophthalic Acid
Authors: McDonald Richard N. , Reineke Charles E.
Published: November 2003

trans
‐1,2‐Dihydrophthalic Acid

product:
trans
‐1,2‐Dihydrophthalic acid
N,N
‐Dimethyldodecylamine Oxide
Authors: Sheng M. N. , Zajacek J. G.
Published: November 2003

N,N
‐dimethyldodecylamine oxide

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

product:
N,N
‐dimethyldodecylamine oxide
1,3‐Dithiane
Authors: Corey E. J. , Seebach D.
Published: November 2003

1,3‐Dithiane

product: 1,3‐dithiane
2,2′‐Dithienyl Sulfide
Authors: Jones E. , Moodie I. M.
Published: November 2003

2,2′‐Dithienyl sulfide

product: 2,2′‐dithienyl sulfide

product: 3,3′‐dithienyl sulfide
Ethyl 1‐Naphthylacetate
Authors: Lee Ving , Newman Melvin S.
Published: November 2003

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

Δ9,10‐octalin

solvent: 250 ml. of anhydrous ethylamine

product: Δ9,10‐octalin

byproduct: Δ1,9‐octalin

product: dimethylamine

product: 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

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
Trimethylsilyl Azide
Authors: Birkofer L. , Wegner P.
Published: November 2003

Trimethylsilyl azide

solvent: 500 ml. of freshly distilled diethylene glycol dimethyl ether

product: trimethylsilyl azide
Aldehydes from Allylic Alcohols and Phenylpalladium Acetate: 2‐Methyl‐3‐Phenylpropionaldehyde
Authors: Heck R. F.
Published: November 2003

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

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

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

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

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
Carbonyl Cyanide
Authors: Martin E. L.
Published: November 2003

Carbonyl cyanide

solvent: 100 ml. of diethyl phthalate

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

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
Direct Iodination of Polyalkylbenzenes: Iododurene
Authors: Suzuki H.
Published: November 2003

Direct iodination of polyalkylbenzenes: iododurene

product: iododurene

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

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

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

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

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

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

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

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

intermediate: Binor‐S

intermediate: tetrahydro‐Binor‐S

product: diamantane
Dideuteriodiazomethane
Authors: Gassman P. G. , Greenlee W. J.
Published: November 2003

Dideuteriodiazomethane

product: dideuteriodiazomethane

reactant: benzoic acid‐
O
‐
d

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

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

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

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

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

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

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

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

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

[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

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
Allylic Chlorides from Allylic Alcohols: Geranyl Chloride
Authors: Stork Gilbert , Grieco Paul A. , Gregson Michael
Published: November 2003

Allylic chlorides from allylic alcohols: geranyl chloride

product: geranyl chloride

product: neryl chloride
5β‐Cholest‐3‐ene‐5‐Acetaldehyde
Authors: Ireland R. E. , Dawson D. J.
Published: November 2003

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

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

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

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

intermediate: N‐(α‐
Methylbenzylidene
)
methylamine

intermediate: N‐
Methyl
‐2‐
phenyl
‐Δ
2
‐
tetrahydropyridine
Aromatic Hydrocarbons from Aromatic Ketones and Aldehydes: 1,1‐Diphenylethane
Authors: Lipsky Sharon D. , Hall Stan S.
Published: November 2003

Aromatic hydrocarbons from aromatic ketones and aldehydes: 1,1‐diphenylethane

product: 1,1‐diphenylethane
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

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

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

(
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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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
Reductive Coupling of Carbonyls to Alkenes: Adamantylideneadamantane
Authors: Fleming Michael P. , McMurry John E.
Published: November 2003

Reductive coupling of carbonyls to alkenes: adamantylideneadamantane

solvent: petroleum ether

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

Preparation of 4‐alkyl‐and 4‐halobenzoyl chlorides: 4‐pentylbenzoyl chloride

product: 4‐pentylbenzoyl chloride

byproduct: 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

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

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