bluuebunny/crossref_metadata_2025_split huggingface dataset:
(Pentafluorophenyl)Acetonitrile
Authors: Filler Robert , Woods Sarah M. 
Published: November 2003

Abstract

(Pentafluorophenyl)Acetonitrile

intermediate: ethyl cyano(pentafluorophenyl)acetate

product:
(Pentafluorophenyl)acetonitrile

reactant: Hexafluorobenzene was purchased from PCR, Inc., Gainesville, Florida

product: 2,3‐bis(pentafluorophenyl)propionitrile

product: bis(pentafluorophenyl)acetonitrile

product: 2‐(pentafluorophenyl)ethylamine hydrochloride

product: 4,5,6,7‐tetrafluoroindoline
3,3,6,6‐Tetramethoxy‐1,4‐Cyclohexadiene
Authors: Margaretha Paul , Tissot Paul 
Published: November 2003

Abstract

3,3,6,6‐Tetramethoxy‐1,4‐cyclohexadiene

product: 3,3,6,6‐tetramethoxy‐1,4‐cyclohexadiene
p
‐Tolylsulfonylmethyl Isocyanide
Authors: Hoogenboom B. E. , Oldenziel O. H. , van Leusen A. M. 
Published: November 2003

Abstract

p
‐Tolylsulfonylmethyl isocyanide

intermediate:
N
‐(
p
‐tolylsulfonylmethyl)formamide

solvent: One liter of petroleum ether

product:
p
‐tolylsulfonylmethyl isocyanide
Arene Oxide Synthesis: Phenanthrene‐9,10‐Oxide
Authors: Cortez Cecilia , Harvey Ronald G. 
Published: November 2003

Abstract

ARENE OXIDE SYNTHESIS: PHENANTHRENE‐9,10‐OXIDE

intermediate: trans‐9,10‐
Dihydro
‐9,10‐
phenanthrenediol
(1)

product:
Phenanthrene
‐9,10‐
oxide
(2)
Catalytic Osmium Tetroxide Oxidation of Olefins:cis‐1,2‐Cyclohexanediol
Authors: VanRheenen V. , Cha D. Y. , Hartley W. M. 
Published: November 2003

AbstractCatalytic osmium tetroxide oxidation of olefins:cis‐1,2‐cyclohexanediolproduct: cis‐1,2‐Cyclohexanediol(2)intermediate:N‐MethylmorpholineN‐oxide (1) can also be purchased from Eastman Organic Chemicals or Fluka A G
Copper Catalyzed Arylation of β‐Dicarbonyl Compounds: 2‐(1‐Acetyl‐2‐Oxopropyl)Benzoic Acid
Authors: Bruggink Alle , Ray Stephen J. , McKillop Alexander 
Published: November 2003

Abstract

Copper catalyzed arylation of β‐dicarbonyl compounds: 2‐(1‐acetyl‐2‐oxopropyl)benzoic acid

reactant: Commercial 2‐bromobenzoic acid, purchased from Aldrich Chemical Company, Inc.

product: 2‐(1‐Acetyl‐2‐oxopropyl)benzoic acid

byproduct: 2‐ethoxybenzoic acid

reactant: 2‐bromobenzoic acid
γ‐Ketoesters from AldehydesViaDiethyl Acylsuccinates: Ethyl 4‐Oxohexanoate
Authors: Wehrli Pius A. , Chu Vera 
Published: November 2003

Abstractγ‐Ketoesters from aldehydesviadiethyl acylsuccinates: ethyl 4‐oxohexanoateintermediate:Diethyl propionylsuccinateproduct: ethyl 4‐oxohexanoate
γ‐Ketoesters to prepare Cyclic Diketones: 2‐Methyl‐1,3‐Cyclopentanedione
Authors: Hengartner U. , Chu Vera 
Published: November 2003

Abstract

γ‐Ketoesters to prepare cyclic diketones: 2‐methyl‐1,3‐cyclopentanedione

solvent: 1.4 l. of xylene

product: 2‐methyl‐1,3‐cyclopentanedione
Macrocyclic Polyamines: 1,4,7,10,13,16‐Hexaäzacycloöctadecane
Authors: Atkins T. J. , Richman J. E. , Oettle W. F. 
Published: November 2003

Abstract

Macrocyclic polyamines: 1,4,7,10,13,16‐hexaäzacycloöctadecane

intermediate: N,N′,N″‐
Tris
(p‐
tolylsulfonyl
)
diethylenetriamine
(1)

intermediate: N,N′,N″‐
Tris
(p‐
tolysulfonyl
)
diethylenetriamine
‐N,N″‐
disodium salt
(2)

intermediate: 3,6,9‐
Tris
(p‐
tolylsulfonyl
)‐3,6,9‐
triazaundecane
‐1,11‐
diol
(3)

intermediate: 3,6,9‐
Tris
(p‐
tolylsulfonyl
)‐3,6,9‐
triazaundecane
‐1,11‐
dimethanesulfonate
(4)

intermediate: 1,4,7,10,13,16‐
Hexakis
(p‐
tolylsulfonyl
)‐1,4,7,10,13,16‐
hexaäzacycloöctadecane
(5)

product: 1,4,7,10,13,16‐hexaäzacycloöctadecane (6)
Macrolides from Cyclization of ω‐Bromocarboxylic Acids: 11‐Hydroxyundecanoic Lactone
Authors: Galli C. , Mandolini L. 
Published: November 2003

Abstract

Macrolides from cyclization of ω‐bromocarboxylic acids: 11‐hydroxyundecanoic lactone

product: 11‐hydroxyundecanoic lactone

product: 1,13‐dioxacyclotetracosane‐2,14‐dione

product: 15‐hydroxypentadecanoic lactone

product: 17‐hydroxyheptadecanoic lactone
Nitriles from Ketones: Cyclohexanecarbonitrile
Authors: Wender P. A. , Eissenstat M. A. , Sapuppo N. , Ziegler F. E. 
Published: November 2003

Abstract

Nitriles from ketones: cyclohexanecarbonitrile

intermediate:
Methyl
2‐(1‐
cyanocyclohexyl)hydrazine carboxylate
(1)

intermediate:
Methyl
2‐(1‐
cyancyclohexyl)diaxenecarboxylate
(2)

product: cyclohexanecarbonitrile (3)
Nucleophilic α‐
sec
‐Aminoalkylation: 2‐(Diphenylhydroxymethyl)pyrrolidine
Authors: Enders D. , Pieter R. , Renger B. , Seebach D. 
Published: November 2003

Abstract

Nucleophilic α‐
sec
‐aminoalkylation: 2‐(Diphenylhydroxymethyl)pyrrolidine

product: 2‐(Diphenylhydroxymethyl)pyrrolidine

reactant: 4 g. (0.05 mole) of ethyl nitrite

reactant: 2.35 g. (0.0331 mole) of pyrrolidine

reactant: 3.44 g. (4.76 ml., 0.0341 mole) of diisopropylamine

reactant: 5.46 g. (0.0300 mole) of benzophenone in 12 ml. of tetrahydrofuran
3‐Trimethylsilyl‐3‐Buten‐2‐One as
M
ichael Acceptor for Conjugate Addition‐Annelation:
cis
‐4,4
a
,5,6,7,8‐Hexahydro‐4
a
,5‐Dimethyl‐2(3
H
)‐Naphthalenone
Authors: Boeckman Robert K. , Blum David M. , Ganem Bruce 
Published: November 2003

Abstract

3‐Trimethylsilyl‐3‐buten‐2‐one as michael acceptor for conjugate addition‐annelation:
cis
‐4,4
a
,5,6,7,8‐hexahydro‐4
a
,5‐dimethyl‐2(3
H
)‐naphthalenone

product:
cis
‐4,4
a
,5,6,7,8‐HEXAHYDRO‐4
a
,5‐DIMETHYL‐2(3
H
)‐NAPHTHALENONE
Conjugate Reduction of α,β‐Unsaturated
p
‐Toluenesulfonylhydrazones to Alkenes with Catecholborane: 5β‐Cholest‐3‐Ene
Authors: Kabalka George W. , Hutchins Robert , Natale Nicholas R. , Yang Dominic T. C. , Broach Vicky 
Published: November 2003

Abstract

Conjugate reduction of α,β‐unsaturated
p
‐toluenesulfonylhydrazones to alkenes with catecholborane: 5β‐cholest‐3‐ene

intermediate: cholest‐4‐en‐3‐one
p
‐toluenesulfonylhydrazone

product: 5β‐cholest‐3‐ene

product: C
6
H
5
CH
2
CHCHCH
3

product: C
6
H
5
CH
2
CHCH
2

product: (CH
3
)
2
CHCHCHCH
3

product: CH
3
(CH
2
)
3
CHCCHCH
3

product: CH
3
CHCCHC
6
H
5

byproduct: 5β‐cholestane

byproduct: 5α‐cholestane

byproduct: 5α‐cholest‐3‐ene
α,β‐Dehydrogenation of β‐Dicarbonyl Compounds by Selenoxide Elimination: 2‐Acetyl‐2‐Cyclohexen‐1‐One
Authors: Renga James M. , Reich Hans J. 
Published: November 2003

Abstract

α,β‐dehydrogenation of β‐dicarbonyl compounds by selenoxide elimination: 2‐acetyl‐2‐cyclohexen‐1‐one

intermediate: 2‐acetyl‐2‐phenylselenocyclohexanone

product: 2‐acetyl‐2‐cyclohexen‐1‐one

reactant: benzeneseleninic acid
Highly Reactive Magnesium for the Preparation of
G
rignard Reagents: 1‐Norbornanecarboxylic Acid
Authors: Rieke Reuben D. , Bales Stephen E. , Hudnall Phillip M. , Burns Timothy P. , Poindexter Graham S. 
Published: November 2003

Abstract

Highly reactive magnesium for the preparation of Grignard reagents: 1‐norbornanecarboxylic acid

intermediate: 2,2‐dichloronorbornane

intermediate: 1‐chloronorbornane

product: 1‐norbornanecarboxylic acid
NucleophilicAcylation with Disodium Tetracarbonylferrate: Methyl 7‐Oxoheptanoate and Methyl 7‐Oxoöctanoate
Authors: Finke Richard G. , Sorrell Thomas N. 
Published: November 2003

Abstract

Nucleophilic Acylation with Disodium Tetracarbonylferrate: Methyl 7‐Oxoheptanoate and Methyl 7‐Oxoöctanoate

intermediate: Disodium tetracarbonylferrate sesquidioxanate

product:
Methyl
7‐
oxoheptanoate

product:
Methyl
7‐
oxo
ö
ctanoate

reactant: Methyl 6‐bromohexanoate
Pentafluorophenylcopper Tetramer, A Reagent for Synthesis of Fluorinated Aromatic Compounds
Authors: Cairncross Allan , Sheppard William A. , Wonchoba Edward 
Published: November 2003

AbstractPentafluorophenylcopper tetramer, a reagent for synthesis of fluorinated aromatic compoundsintermediate: bis(pentafluorophenylcopper)dioxane complexproduct: pentafluorophenylcopper tetramersolvent: dioxaneproduct: C6F5Cu·benzonitrileproduct: C6F5Cu·tributylamineproduct: (C6F5Cu)2·dioxaneproduct: C6F5Cu·quinolineproduct: (C6F5Cu)2·1,5‐cycloöctadieneproduct: C6F5Cu·dimethylacetyleneproduct: (C6F5Cu)2·butadieneproduct: C6F5Cu·tetraethylammonium cyanideproduct: C6F5Hproduct: C6F5‐C6F5product: C6F5Br(4) + C6F5‐C6F5product: C6F5‐C6F5product: CH3‐C6F5product: C6H5CH2C6F5product: 1‐pentafluorophenylbicyclo[2.2.2]octaneproduct: (C2H5O2)CCH2C6F5product: C6F5‐C6H5product: 3‐FC6H4‐C6F5product: O2NC6H4C6F5metaproduct: 4‐(CH3)2NC6H4C6F5product: 4‐C2H5O2CC6H4C6F5product: C6F5CFCF2product: C6F5CCC6F5product: C6H5‐C6F5product: (C2H5)3SiCCC6F5product:(Pentafluorophenyl)benzeneproduct: 1‐(Pentafluorophenyl)adamantane
Reagents for Synthesis of Organoselenium Compounds: Diphenyl Diselenide and Benzeneselenenyl Chloride
Authors: Reich Hans J. , Cohen Martin L. , Clark Peter S. 
Published: November 2003

Abstract

Reagents for synthesis of organoselenium compounds: diphenyl diselenide and benzeneselenenyl chloride

product: diphenyl diselenide

product: benzeneselenenyl chloride

product: C
6
H
5
SeBr

product: C
6
H
5
SeNa

product: C
6
H
5
SeH
Tertiary Alcohols from Hydrocarbons by Ozonation on Silica Gel: 1‐Adamantanol
Authors: Cohen Zvi , Varkony Haim , Keinan Ehud , Mazur Yehuda 
Published: November 2003

Abstract

Tertiary alcohols from hydrocarbons by ozonation on silica gel: 1‐adamantanol

product: adamantanol

product: 1,3‐adamantanediol
Thiol Protection with the Acetamidomethyl Group:
S
‐Acetamidomethyl‐
L
‐Cysteine Hydrochloride
Authors: Milkowski John D. , Veber Daniel F. , Hirschmann Ralph 
Published: November 2003

Abstract

Thiol protection with the acetamidomethyl group:
S
‐acetamidomethyl‐
L
‐cysteine hydrochloride

intermediate:
N
‐(hydroxymethyl)acetamide

product:
S
‐acetamidomethyl‐
L
‐cysteine hydrochloride

byproduct:
S
‐acetamidomethyl‐
L
‐cysteine monohydrate
Homoconjugate Addition of Nucleophiles to Cyclopropane‐1,1‐Dicarboxylate Derivatives: 2‐Oxo‐1‐Phenyl‐3‐Pyrrolidinecarboxylic Acid
Authors: Singh Rajendra K. , Danishefsky Samuel 
Published: November 2003

Abstract

Homoconjugate addition of nucleophiles to cyclopropane‐1,1‐dicarboxylate derivatives: 2‐Oxo‐1‐phenyl‐3‐pyrrolidinecarboxylic acid

intermediate: 6,6‐Dimethyl‐5,7‐dioxaspiro[2.5]octane‐4,8‐dione

product: 2‐Oxo‐1‐phenyl‐3‐pyrrolidinecarboxylic acid (3)

intermediate: cyclopropane‐1,1‐dicarboxylic acid

intermediate: 1‐cyanocyclopropanecarboxylic acid

intermediate: 1‐acetylcyclopropanecarboxylic acid
Methylene Ketones and Aldehydes by Simple, Direct Methylene Transfer: 2‐Methylene‐1‐Oxo‐1,2,3,4‐Tetrahydronaphthalene
Authors: Gras Jean‐Louis 
Published: November 2003

Abstract

Methylene ketones and aldehydes by simple, direct methylene transfer: 2‐methylene‐1‐oxo‐1,2,3,4‐tetrahydronaphthalene

product: 2‐METHYLENE‐1‐OXO‐1,2,3,4‐TETRAHYDRONAPHTHALENE

reactant: 16.57 g (0.075 mol) of
N
‐methylanilinium trifluoroacetate
2‐Phenyl‐2‐Adamantanamine Hydrochloride
Authors: Kalir Asher , Balderman David 
Published: November 2003

Abstract

2‐Phenyl‐2‐adamantanamine hydrochloride

reactant: 22.8 g (0.1 mol) of 2‐phenyl‐2‐adamantanol

intermediate: 24 g (0.095 mol) of the crude 2‐azido‐2‐phenyladamantane

product: 2‐phenyl‐2‐adamantanamine hydrochloride

product: 2‐butyl‐2‐adamantanamine hydrochloride
Trimethylsilyl Cyanide: Cyanosilation of
p
‐Benzoquinone
Authors: Livinghouse Tom 
Published: November 2003

Abstract

Trimethylsilyl cyanide: Cyanosilation of
p
‐benzoquinone

intermediate: trimethylsilyl cyanide

product:
p
‐Benzoquinone monotrimethylsilyl cyanohydrin
Chiral Media for Asymmetric Solvent Inductions. (
S,S
)‐( + )‐1,4‐Bis(dimethylamino)‐2,3‐dimethoxybutane from (
R,R
)‐( + )‐Diethyl Tartrate
Authors: Seebach Dieter , Kalinowski Hans‐Otto , Langer Werner , Crass Gerhard , Wilka Eva‐Maria 
Published: November 2003

Abstract

Chiral media for asymmetric solvent inductions. (
S,S
)‐( + )‐1,4‐Bis(dimethylamino)‐2,3‐dimethoxybutane from (
R,R
)‐( + )‐diethyl tartrate

intermediate: (R,R)‐( + )‐N,N,N′,N′‐Tetramethyltartaric acid diamide

reactant: 450 mL (7 mol) of liquid, anhydrous, cold (− 78°C) dimethylamine

intermediate: (R,R)‐( + )‐2,3‐Dimethoxy‐N,N,N′,N′‐tetramethylsuccinic acid diamide

product: (S,S)‐( + )‐1,4‐Bis (dimethylamino)‐2,3‐dimethoxybutane (DDB)

reactant: (R,R)‐( + )‐diethyl tartrate

reactant: (R,R)‐( + )‐tartaric acid (Firma Benckiser, D‐Ludwigshafen, or Firma Boehringer, D‐Ingelheim)
Cyanic Acid Esters from Phenols: Phenyl Cyanate
Authors: Martin D. , Bauer M. 
Published: November 2003

AbstractCyanic acid esters from phenols: phenyl cyanateproduct: phenyl cyanateproduct: 2‐CH3C6H4OCNproduct: 4‐CH3C6H4OCNproduct: 4‐CH3OC6H4OCNproduct: 2‐ClC6H4OCNproduct: 4‐ClC6H4OCNproduct: 2‐CH3OCOC6H4OCNproduct: 2‐Naphthyl‐OCNproduct: 4‐NCOC6H4OCNproduct: CCl3CH2OCNproduct: CF3CH2OCN
Alkylation of the Anion from Birch Reduction of
o
‐Anisic Acid: 2‐Heptyl‐2‐Cyclohexenone
Authors: Taber D. F. , Gunn B. P. , Chiu I‐Ching 
Published: November 2003

Abstract

Alkylation of the anion from birch reduction of
o
‐anisic acid: 2‐heptyl‐2‐cyclohexenone

product: 2‐heptyl‐2‐cyclohexenone
Perhydro‐9b‐Boraphenalene and Perhydro‐9b‐Phenalenol
Authors: Negishi Ei‐ichi , Brown Herbert C. 
Published: November 2003

Abstract

Perhydro‐9b‐boraphenalene and perhydro‐9b‐phenalenol

intermediate:
cis,cis,trans
‐2‐(perhydro‐9′b‐phenalyl)‐1,3,2‐dioxaborole

product:
cis,cis,trans
‐perhydro‐9b‐phenalenol

product:
cis,trans
‐ and
cis,cis
‐perhydro‐9b‐boraphenalene
Photoprotonation of Cycloalkenes: Limonene to
p
‐Menth‐8‐en‐1‐yl Methyl Ether
Authors: Tise F. P. , Kropp P. J. 
Published: November 2003

Abstract

Photoprotonation of cycloalkenes: limonene to
p
‐menth‐8‐en‐1‐yl methyl ether

product:
cis
‐ and
trans
‐
p
‐menth‐8‐en‐1‐yl methyl ether

product: cyclohexyl methyl ether in 70% yield
Silylation of Ketones With Ethyl Trimethylsilacetate: (Z)‐3‐Trimethylsiloxy‐2‐Pentene
Authors: Kuwajima Isao , Nakamura Eiichi , Hashimoto Koichi 
Published: November 2003

Abstract

Silylation of ketones with ethyl trimethylsilacetate: (Z)‐3‐trimethylsiloxy‐2‐pentene

intermediate: ethyl trimethylsilylacetate

product: 3‐trimethylsiloxy‐2‐pentene
Generation and Reactions of Alkenyllithium Reagents: 2‐Butylbornene
Authors: Chamberlin A. Richard , Liotta Ellen L. , Bond F. Thomas 
Published: November 2003

Abstract

Generation and Reactions of Alkenyllithium Reagents: 2‐Butylbornene

reactant: 30.4 g (0.20 mol) of d‐camphor

product: 2‐Butylbornene

intermediate: 40.0 g (0.092 mol) of d‐camphor 2,4,6‐triisopropylbenzenesulfonylhydrazone

byproduct: bornylene
A General Synthetic Method for the Preparation of Methyl Ketones from Terminal Olefins: 2‐Decanone
Authors: Tsuji Jiro , Nagashima Hideo , Nemoto Hisao 
Published: November 2003

Abstract

A General synthetic method for the preparation of methyl ketones from terminal olefins: 2‐decanone

product: 2‐decanone
cis‐N
‐Tosyl‐3‐Methyl‐2‐Azabicyclo[3.3.0]Oct‐3‐Ene
Authors: Hegedus Louis S. , Holden Michael S. , McKearin James M. 
Published: November 2003

Abstract

cis
‐
N
‐tosyl‐3‐methyl‐2‐azabicyclo[3.3.0]oct‐3‐ene

reactant: 20.0 g (158 mmol) of
trans
‐2‐(2‐propenyl)cyclopentanol

reactant: 8.00 g (64 mmol) of
cis
‐2‐(2‐propenyl)cyclopentylamine

product:
cis‐N‐Tosyl‐3‐methyl‐2‐azabicyclo[3.3.0]oct‐3‐ene
.

reactant: 5.159 g (18.49 mmol) of
cis
‐1‐
N
‐tosyl‐2‐(2‐propenyl)cyclopentylamine

catalyst: Palladium(II) chloride–acetonitrile complex
Silylation of 2‐Methyl‐2‐Propen‐1‐ol Dianion: 2‐(Hydroxymethyl)Allyltrimethylsilane
Authors: Trost Barry M. , Chan Dominic M. T. , Nanninga Thomas N. 
Published: November 2003

Abstract

Silylation of 2‐methyl‐2‐propen‐1‐ol dianion: 2‐(hydroxymethyl)allyltrimethylsilane

intermediate: 4.25 g, bp 29–57°C (4 mm), and 45.8 g (52%) of 2‐(trimethylsiloxy)allyltrimethylsilane

product: 0.4 g, bp 22–54°C (4 mm), and 10.95 g (78%) of 2‐(hydroxymethyl)allyltrimethylsilane

byproduct: mineral oil

byproduct: 4–6% of a vinylsilane
Conjugate Allylation of α,β‐Unsaturated Ketones with Allylsilanes: 4‐Phenyl‐6‐Hepten‐2‐one
Authors: Sakurai Hideki , Hosomi Akira , Hayashi Josabro 
Published: November 2003

Abstract

Conjugate allylation of α,β‐unsaturated ketones with allylsilanes: 4‐phenyl‐6‐hepten‐2‐one

product: 4‐phenyl‐6‐hepten‐2‐one

product: 1‐methyl‐1‐trimethylsilylmethyl‐3‐n‐propylspiro[3,4]octan‐5‐one

product: 2,8a‐diallyl‐3,4,4a,5,6,7,8,8a‐octahydronaphthalene

product: CH
2
CH(CH
2
)
3
COCH
3

product: CH
2
C(CH
3
)
2
CH
2
CH
2
COCH
3

product: CH
2
CHCH
2
C(CH
3
)
2
CH
2
COCH
3

product: CH
2
C(CH
3
)CH
2
CH(Ph)CH
2
COCH
3

product: CH
2
CHCH(CH
3
)CH(Ph)CH
2
COCH
3

product: CH
2
CHCH
2
CH(Ph)CH
2
COCH
3
β‐Haloacetals and Ketals: 2‐(2‐Bromoethyl)‐1,3‐dioxane and 2,5,5‐Trimethyl‐2‐(2‐bromoethyl)‐1,3‐dioxane
Authors: Stowell J. C. , Keith D. R. , King B. T. 
Published: November 2003

Abstract

β‐Haloacetals and ketals: 2‐(2‐bromoethyl)‐1,3‐dioxane and 2,5,5‐trimethyl‐2‐(2‐bromoethyl)‐1,3‐dioxane

product: 2‐(2‐Bromoethyl)‐1,3‐dioxane

product: 2,5,5‐Trimethyl‐2‐(2‐bromoethyl)‐1,3‐dioxane

unknown: 1,9‐diphenylnona‐1,3,6,8‐tetraen‐5‐one

intermediate: 3‐bromopropanal

intermediate: 4‐bromo‐2‐butanone
Cycloundecanecarboxylic Acid
Authors: Hamada Yasumasa , Shioiri Takayuki 
Published: November 2003

Abstract

Cycloundecanecarboxylic acid

intermediate: 1‐(
N
‐pyrrolidino)‐1‐cyclododecene

product: cycloundecanecarboxylic acid

intermediate: diphenyl (cycloundecyl‐1‐pyrrolidinylmethylene)phosphoramidate
α‐Allenic Esters from α‐Phosphoranylidene Esters and Acid Chlorides: Ethyl 2,3‐Pentadienoate
Authors: Lang Robert W. , Hansen Hans‐Jürgen 
Published: November 2003

Abstract

α‐Allenic esters from α‐phosphoranylidene esters and acid chlorides: Ethyl 2,3‐pentadienoate

reactant: 34.8 g (0.10 mol) of ethyl (triphenylphosphoranylidene)acetate

product: ethyl 2,3‐pentadienoate
Preparation of Chiral, Nonracemic γ‐Lactones by Enzymecatalyzed Oxidation of
meso
‐Diols: ( + )‐(1
R
,6
S
)‐8‐Oxabicyclo[4.3.0]Nonan‐7‐One
Authors: Jones J. Bryan , Jakovac Ignac J. 
Published: November 2003

Abstract

Preparation of chiral, nonracemic γ‐lactones by enzymecatalyzed oxidation of
meso
‐diols: ( + )‐(1
R
,6
S
)‐8‐oxabicyclo[4.3.0]nonan‐7‐one

product: ( + )‐(1
R
,6
S
)‐8‐oxabicyclo[4.3.0]nonan‐7‐one
Enantioselective Epoxidation of Allylic Alcohols: (2
S
,3
S
)‐3‐Propyloxiranemethanol
Authors: Hill J. Gordon , Sharpless K. Barry , Exon Christopher M. , Regenye Ronald 
Published: November 2003

Abstract

Enantioselective epoxidation of allylic alcohols: (2
S
,3
S
)‐3‐propyloxiranemethanol

product: (2
S
,3
S
)‐3‐propyloxiranemethanol
(2
SR
,3
RS
)‐2,4‐Dimethyl‐3‐hydroxypentanoic Acid
Authors: Bal B. , Buse C. T. , Smith K. , Heathcock Clayton H. 
Published: November 2003

Abstract

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

solvent: 31 mL (0.22 mol) of diisopropylamine

solvent: 14.4 g (0.20 mol) of 2‐methylpropanal

intermediate: 12.0 g of 5‐hydroxy‐2,4,6‐trimethyl‐2‐(trimethylsiloxy)heptan‐3‐one (10.8 g, 41 mmol of ketone from a 90 : 10 mixture from Part A)

product: (2
SR
,3
RS
)‐2,4‐dimethyl‐3‐hydroxypentanoic acid

intermediate: α,γ,γ‐trimethylbutyrolactone
(
S
)‐(+)‐γ‐Butyrolactone‐γ‐carboxylic Acid
Authors: Gringore Olivier H. , Rouessac Francis P. 
Published: November 2003

Abstract

(
S
)‐(+)‐γ‐butyrolactone‐γ‐carboxylic acid

reactant: 294 g (2 mol) of L‐glutamic acid

product: (+)‐γ‐butyrolactone‐γ‐carboxylic acid
2,3‐
O
‐Isopropylidene‐
D
‐Erythronolactone
Authors: Cohen Noal , Banner Bruce L. , Laurenzano Anthony J. , Carozza Louis 
Published: November 2003

Abstract

2,3‐
O
‐isopropylidene‐
D
‐erythronolactone

intermediate:
D
‐erythronolactone

product: 2,3‐
O
‐isopropylidene‐
D
‐erythronolactone
tert‐Butoxycarbonylation of Amino Acids and their Derivatives:N‐tert‐Butoxycarbonyl‐l‐phenylalanine
Authors: Keller Oskar , Keller Walter E. , Look Gert van , Wersin Gernot 
Published: November 2003

Abstracttert‐Butoxycarbonylation of amino acids and their derivatives:N‐tert‐butoxycarbonyl‐l‐phenylalaninereactant: 223 g (1 mol) of di‐tert‐butyl dicarbonateproduct: N‐tert‐butoxycarbonyl‐L‐phenylalanineproduct: Boc‐Ala‐OHproduct: Boc‐β‐Ala‐OHproduct: Boc‐Arg‐OHproduct: Boc‐Arg(NO2)‐OHproduct: Boc‐Asn‐OHproduct: Boc‐Asp(OBzl)‐OHproduct: Boc‐Cys(Bzl)‐OHproduct: (Boc‐Cys‐OH)2product: Boc‐Gln‐OHproduct: Boc‐Glu(OBzl)‐OHproduct: Boc‐Gly‐OHproduct: Boc‐His(Boc)‐OHproduct: Boc‐Ile‐OHproduct: Boc‐Leu‐OHproduct: Boc‐Lys(Boc)‐OHproduct: Boc‐Lys(CBZ)‐OHproduct: Boc‐Met‐OHproduct: Boc‐Met‐OHproduct: Boc‐Pro‐OHproduct: Boc‐Ser‐OHproduct: Boc‐Ser(Bzl)‐OHproduct: Boc‐Thr‐OHproduct: Boc‐Trp‐OHproduct: Boc‐Trp‐(FOR)‐OHproduct: Boc‐Tyr‐OHproduct: Boc‐Tyr‐OHproduct: Boc‐Tyr(Bzl)‐OHproduct: Boc‐Tyr(2,6‐Cl2‐Bzl)‐OHproduct: Boc‐Val‐OH
N‐
tert
‐Butoxycarbonyl‐l‐phenylalanine
Authors: Paleveda William J. , Holly Frederick W. , Veber Daniel F. 
Published: November 2003

Abstract

N‐
tert
‐butoxycarbonyl‐l‐phenylalanine

product: tert‐butoxycarbonyl‐L‐phenylalanine
Esterification of Carboxylic Acids with Dicyclohexylcarbodiimide/4‐Dimethylaminopyridine:tert‐Butyl Ethyl Fumarate
Authors: Neises B. , Steglich Wolfgang 
Published: November 2003

AbstractEsterification of carboxylic acids with dicyclohexylcarbodiimide/4‐dimethylaminopyridine:tert‐butyl ethyl fumaratereactant: 45.59 g (0.22 mol) of dicyclohexylcarbodiimideproduct: tert‐butyl ethyl fumarate
Anodic Oxidation of
N
‐Carbomethoxypyrrolidine: 2‐Methoxy‐
N
‐Carbomethoxypyrrolidine
Authors: Shono T. , Matsumura Y. , Tsubata K. 
Published: November 2003

Abstract

Anodic oxidation of
N
‐carbomethoxypyrrolidine: 2‐methoxy‐
N
‐carbomethoxypyrrolidine

intermediate: 119–121 g (92–94%) of
N
‐carbomethoxypyrrolidine, bp 64°C/1.3 mm

product:
2‐Methoxy‐N‐carbomethoxypyrrolidine
.

byproduct:
N
‐carbomethoxy‐2,5‐dimethoxypyrrolidine
Conversion of Methyl Ketones into Terminal Alkynes: (
E
)‐Buten‐3‐ynyl‐2,6,6‐trimethyl‐1‐cyclohexene
Authors: Negishi Ei‐ichi , King Anthony O. , Tour James M. 
Published: November 2003

Abstract

Conversion of methyl ketones into terminal alkynes: (
E
)‐buten‐3‐ynyl‐2,6,6‐trimethyl‐1‐cyclohexene

product: (E)‐buten‐3‐ynyl‐2,6,6‐trimethyl‐1‐cyclohexene
β‐Dimethylaminomethylenation:
N,N
‐Dimethyl‐
N
′‐
p
‐tolylformamidine
Authors: Gupton John T. , Andrews Steven A. 
Published: November 2003

Abstract

β‐Dimethylaminomethylenation:
N,N
‐dimethyl‐
N
′‐
p
‐ tolylformamidine

intermediate: [3‐(Dimethylamino)‐2‐azaprop‐2‐en‐1‐ylidene]dimethylammonium chloride

product:
N,N
‐dimethyl‐
N
′‐
p
‐tolylformamidine
1,3‐Dimethylimidazole‐2‐thione
Authors: Benac Brian L. , Burgess Edward M. , Arduengo Anthony J. 
Published: November 2003

Abstract

1,3‐Dimethylimidazole‐2‐thione

reactant: 44.8 g (0.20 mol) of 1,3‐dimethylimidazolium iodide

product: 1, 3‐dimethylimidazole‐2‐thione
(
S
)‐( + )‐2‐(
p
‐Toluenesulfinyl)‐2‐Cyclopentenone: Precursor for Enantioselective Synthesis of 3‐Substituted Cyclopentanones
Authors: Hulce Martin , Mallomo John P. , Frye Leah L. , Kogan Timothy P. , Posner Gary H. 
Published: November 2003

Abstract

(
S
)‐( + )‐2‐(
p
‐toluenesulfinyl)‐2‐cyclopentenone: Precursor for enantioselective synthesis of 3‐substituted cyclopentanones

intermediate: 57.5 g of crude methyl
p
‐toluenesulfinate

intermediate: (
S
)‐( + )‐2‐(
p
‐toluenesulfinyl)‐2‐cyclopentenone ethylene ketal

product: (
S
)‐( + )‐2‐(
p
‐toluenesulfinyl)‐2‐cyclopentenone
Tosylhydrazone Salt Pyrolyses: Phenyldiazomethanes
Authors: Creary Xavier 
Published: November 2003

Abstract

Tosylhydrazone salt pyrolyses: phenyldiazomethanes

intermediate: benzaldehyde tosylhydrazone

product: phenyldiazomethane

product: p‐MeC
6
H
4
CHN
2

product: m‐MeC
6
H
4
CHN
2

product: p‐FC
6
H
4
CHN
2

product: m‐FC
6
H
4
CHN
2
3,3‐Dimethyl‐1,5‐Diphenylpentane‐1,5‐dione
Authors: Narasaka Koichi 
Published: November 2003

Abstract

3,3‐Dimethyl‐1,5‐diphenylpentane‐1,5‐dione

intermediate: isopropylideneacetophenone

catalyst: Titanium tetrachloride (7.7 mL)

product: 3,3‐dimethyl‐1,5‐diphenylpentane‐1,5‐dione
Methylenation of Carbonyl Compounds: (+)‐3‐Methylene‐
cis
‐
p
‐methane
Authors: Lombardo Luciano 
Published: November 2003

Abstract

Methylenation of carbonyl compounds: (+)‐3‐Methylene‐
cis
‐
p
‐methane

intermediate: (+)‐isomenthone

product: (+)‐3‐methylene‐
cis
‐
p
‐menthane