bluuebunny/crossref_metadata_2025_split huggingface dataset:
Propargylation of Alkyl Halides: (
E
)‐6,10‐dimethyl‐5,9‐undecadien‐1‐yne and (
E
)‐7,11‐dimethyl‐6,10‐dodecadien‐2‐yn‐1‐ol
Authors: Hooz John , Cabezas Jorge , Musmanni Sergio , Calzada Jose 
Published: November 2003

Abstract

Propargylation of alkyl halides: (
E
)‐6,10‐dimethyl‐5,9‐undecadien‐1‐yne and (
E
)‐7,11‐dimethyl‐6,10‐dodecadien‐2‐yn‐1‐ol

product: (E)‐6,10‐dimethyl‐5,9‐undecadien‐1‐yne

byproduct: 2‐butyn‐1‐ol

product: (E)‐7,11‐dimethyl‐6,10‐dodecadien‐2‐yn‐1‐ol

reactant: trimethylsilyl‐protected acetylene
N
‐Fluoropyridinium Triflate: An Electrophilic Fluorinating Agent
Authors: Umemoto Teruo , Tomita Kyoichi , Kawada Kosuke 
Published: November 2003

Abstract

N
‐fluoropyridinium triflate: an electrophilic fluorinating agent

reactant: 10.3 g (0.06 mol) of sodium triflate

intermediate: N‐fluoropyridinium triflate

intermediate: 3‐Methoxy‐17‐trimethylsiloxy‐1,3,5(10), 16‐estratetraene.

reactant: 6.8 g (0.024 mol) of estrone 3‐methyl ether

product: 16α‐fluoroestrone 3‐methyl ether

byproduct: 16β‐fluoroestrone

byproduct: 2‐pyridyl triflate

product: n‐C12H25F

product: CHF(COOEt)2

product: CF2(COOEt)2

product: CHF(COOEt)2

product: p‐ClC6H4SCH2F

product: Ph‐F

product: F‐C6H4OH (o:p)

product: o‐F‐C6H4OH

product: F‐C6H4NHCOOEt (o:p)

product: F‐C6H4NHCOOEt (o:p)

product: PhCH(OAc)CH2F
Methyl 2‐Chloro‐2‐Cyclopropylidenacetate
Authors: Liese Thomas , Seyed‐Mahdavi Fereydoun , de Meijere Armin 
Published: November 2003

Abstract

Methyl 2‐chloro‐2‐cyclopropylidenacetate

intermediate: trimethyl 2‐chloro‐2‐cyclopylidenorthoacetate

product: methyl 2‐chloro‐2‐cyclopropylidenacetate

product: ethyl 2‐cyclopropylidenacetate
A General Synthesis of Cyclobutanones from Olefins and Tertiary Amides: 3‐Hexylcyclobutanone
Authors: Schmit C. , Falmagne J. B. , Escudero J. , Vanlierde H. , Ghosez L. 
Published: November 2003

Abstract

A general synthesis of cyclobutanones from olefins and tertiary amides: 3‐Hexylcyclobutanone

product: 3‐hexylcyclobutanone
7‐Chloro‐7‐Cyanobicyclo[4.2.0]Octan‐8‐one
Authors: Fishbein Paul L. , Moore Harold W. 
Published: November 2003

Abstract

7‐Chloro‐7‐cyanobicyclo[4.2.0]octan‐8‐one

reactant: 50.7 g (0.30 mol) of mucochloric acid

product: 7‐Chloro‐7‐cyanobicyclo[4.2.0]octan‐8‐one.

intermediate: 20.0 g (94.8 mmol) of 3,4‐dichloro‐5‐isopropoxy‐2(5H)‐furanone

intermediate: azidofuranone

solvent: petroleum ether

product: 2‐azetidinone
Rearrangement of 4‐Aryl‐4‐hydroxy‐2,3‐dialkoxycyclobutenones to Annulated Hydroquinones and Quinones: 5,6‐Diethoxybenzofuran‐4,7‐dione
Authors: Perri S. T. , Rice P. , Moore H. W. 
Published: November 2003

Abstract

Rearrangement of 4‐aryl‐4‐hydroxy‐2,3‐dialkoxycyclobutenones to annulated hydroquinones and quinones: 5,6‐Diethoxybenzofuran‐4,7‐dione

product: 5,6‐diethoxybenzofuran‐4,7‐dione

reactant: 9.00 g (52.9 mmol) of diethyl squarate
(R)‐(−)‐10‐Methyl‐1(9)‐Octal‐2‐One
Authors: Revial G. , Pfau M. 
Published: November 2003

Abstract

(R)‐(−)‐10‐methyl‐1(9)‐octal‐2‐one

reactant: 100.0 g (0.825 mol) of (S)‐(−)‐α‐methylbenzylamine

intermediate: (R)‐(+)‐2‐Methyl‐2‐(3‐oxobutyl)cyclohexanone (2)

reactant: 72.5 mL (61.0 g, 0.870 mol, ca. 1.05 equiv) of freshly distilled methyl vinyl ketone

product: (R)‐(−)‐10‐Methyl‐1(9)‐octal‐2‐one (3)
9‐Borabicyclo[3.3.1]Nonane Dimer
Authors: Soderquist John A. , Negron Alvin 
Published: November 2003

Abstract9‐Borabicyclo[3.3.1]nonane dimerbyproduct: dimethyl sulfideproduct: 9‐borabicyclo[3.3.1]nonane (9‐BBN) dimer
Synthesis of β‐Keto Esters by
C
‐Acylation of Preformed Enolates With Methyl Cyanoformate: Preparation of Methyl (1α,4aβ,8aα)‐2‐Oxodecahydro‐1‐Naphthoate
Authors: Crabtree Simon R. , Mander Lewis N. , Sethi S. Paul 
Published: November 2003

Abstract

Synthesis of β‐keto esters by C‐acylation of preformed enolates with methyl cyanoformate: preparation of methyl (1α,4aβ,8aα)‐2‐oxodecahydro‐1‐naphthoate

product: methyl (1α,4aβ,8aα)‐2‐oxodecahydro‐1‐naphthoate
Oxidation of Secondary Amines to Nitrones: 6‐Methyl‐2,3,4,5‐Tetrahydropyridine N‐Oxide
Authors: Murahashi Shun‐Ichi , Shiota Tatsuki , Imada Yasushi 
Published: November 2003

Abstract

Oxidation of secondary amines to nitrones: 6‐methyl‐2,3,4,5‐tetrahydropyridine N‐oxide

reactant: 23.5 mL (200 mmol) of 2‐methylpiperidine

product: 6‐methyl‐2,3,4,5‐tetrahydropyridine N‐oxide

byproduct: (3,10‐dimethyl‐2,9‐dioxa‐1,8‐diazatricyclo[8.4.0.03,8]tetradecane
Asymmetric Catalytic Glyoxylate‐Ene Reaction: Methyl (2R)‐2‐Hydroxy‐4‐Phenyl‐4‐Pentenoate
Authors: Mikami Koichi , Terada Masahiro , Narisawa Satoshi , Nakai Takeshi 
Published: November 2003

Abstract

Asymmetric catalytic glyoxylate‐ene reaction: methyl (2R)‐2‐hydroxy‐4‐phenyl‐4‐pentenoate

intermediate: Diisopropoxytitanium(IV) dibromide

reactant: methyl glyoxylate (6.16 g, 70.0 mmol)

product: methyl 2‐hydroxy‐4‐phenyl‐4‐pentenoate
Palladium(0)‐Catalyzed Reaction of 9‐Alkyl‐9‐Borabicyclo[3.3.1]Nonane with 1‐Bromo‐1‐Phenylthioethene: 4‐(3‐Cyclohexenyl)‐2‐Phenylthio‐1‐Butene
Authors: Ishiyama Tatsuo , Miyaura Norio , Suzuki Akira 
Published: November 2003

AbstractPalladium(0)‐catalyzed reaction of 9‐alkyl‐9‐borabicyclo[3.3.1]nonane with 1‐bromo‐1‐phenylthioethene: 4‐(3‐cyclohexenyl)‐2‐phenylthio‐1‐buteneintermediate: 1‐bromo‐1‐phenylthioetheneproduct: 4‐(3‐cyclohexenyl)‐2‐phenylthio‐1‐buteneintermediate: 9‐[2‐(3‐cyclohexenyl)ethyl]‐9‐BBN
Ethyl 3‐Oxo‐4‐Pentenoate (
N
azarov's Reagent)
Authors: Zibuck R. , Streiber J. 
Published: November 2003

Abstract

Ethyl 3‐oxo‐4‐pentenoate (Nazarov's reagent)

intermediate: ethyl 3‐hydroxy‐4‐pentenoate

product: ethyl 3‐oxo‐4‐pentenoate
StereoselectiveAldol Reaction of Doubly Deprotonated (R)‐(+)‐2‐Hydroxy‐1,2,2‐Triphenylethyl Acetate (Hytra): (R)‐3‐Hydroxy‐4‐Methylpentanoic Acid
Authors: Braun Manfred , Gräf Silke 
Published: November 2003

Abstract

Stereoselective aldol reaction of doubly deprotonated (R)‐(+)‐2‐hydroxy‐1,2,2‐triphenylethyl acetate (Hytra): (R)‐3‐hydroxy‐4‐methylpentanoic acid

product: (R)‐(+)‐3‐hydroxy‐4‐methylpentanoic acid in 86–92%

solvent: petroleum ether (low‐boiling fraction, bp 30–37°C)

byproduct: (R)‐(+)‐1,1,2‐triphenyl‐1,2‐ethanediol
Synthesis of (S)‐2‐Methylproline: A General Method for the Preparation of α‐Branched Amino Acids
Authors: Beck A. K. , Blank S. , Job K. , Seebach D. , Sommerfeld Th. 
Published: November 2003

AbstractSynthesis of (S)‐2‐methylproline: A general method for the preparation of α‐branched amino acidsintermediate: 20.0 g (0.109 mol) of (2R,5S)‐2‐tert‐butyl‐1‐aza‐3‐oxabicyclo[3.3.0]octan‐4‐oneintermediate: 20.1 g (0.102 mol) of (2R,5S)‐2‐tert‐butyl‐5‐methyl‐1‐aza‐3‐oxabicyclo[3.3.0]octan‐4‐oneproduct: (S)‐2‐methylprolineproduct: (R)‐2‐methylproline
Asymmetric Hydrogenation of Allylic Alcohols Using
BINAP
‐Ruthenium Complexes: (S)‐(−)‐Citronellol
Authors: Takaya Hidemasa , Ohta Tetsuo , Inoue Shin‐ichi , Tokunaga Makoto , Kitamura Masato , Noyori Ryoji 
Published: November 2003

Abstract

Asymmetric hydrogenation of allylic alcohols using BINAP‐ruthenium complexes: (S)‐(−)‐citronellol

intermediate: Ru(OCOCH
3
)
2
[(R)‐binap]

product: (S)‐(−)‐citronellol

byproduct: ruthenium carbonyl complex

byproduct: dihydrocitronellol

reactant: citronellic acid

product: 4,8‐dimethylnon‐7‐enol
Stereospecific Synthesis of Ethyl (Z)‐3‐Bromo‐2‐Propenoate
Authors: Ma Shengming , Lu Xiyan 
Published: November 2003

Abstract

Stereospecific synthesis of ethyl (Z)‐3‐bromo‐2‐propenoate

product: ethyl (2Z)‐3‐bromopropenoate
Indole‐2‐Acetic Acid Methyl Esters: Methyl 5‐Methoxyindole‐2‐Acetate
Authors: Modi Sandeep P. , Oglesby R. Christopher , Archer Sydney 
Published: November 2003

AbstractIndole‐2‐acetic acid methyl esters: methyl 5‐methoxyindole‐2‐acetateintermediate: 5‐methoxy‐2‐nitrophenylacetic acidintermediate: Methyl (5‐methoxy‐2‐nitrophenylacetyl)acetoacetateintermediate: Methyl 4‐(5‐methoxy‐2‐nitrophenyl)‐3‐oxobutyrateproduct: Methyl 5‐methoxyindole‐2‐acetateproduct: methyl (2‐nitrophenylacetyl)acetoacetateproduct: methyl 4‐(2‐nitrophenyl)‐3‐oxobutyrateproduct: methyl indole‐2‐acetate
Manganese‐Copper‐Catalyzed Conjugate Addition of Organomagnesium Reagents to α,β‐Ethylenic Ketones: 2‐(1,1‐Dimethylpentyl)‐5‐Methyl‐Cyclohexanone from Pulegone
Authors: Marquais S. , Alami M. , Cahiez G. 
Published: November 2003

Abstract

Manganese‐copper‐catalyzed conjugate addition of organomagnesium reagents to α,β‐ethylenic ketones: 2‐(1,1‐dimethylpentyl)‐5‐methyl‐cyclohexanone from pulegone

product: 2‐(dimethylpentyl)‐5‐methylcyclohexanone

product: Me2CCHCOMe
Highly Reactive Calcium for the Preparation of Organocalcium Reagents: 1‐Adamantyl Calcium Halides and their Addition to Ketones: 1‐(1‐Adamantyl)Cyclohexanol
Authors: Rieke Reuben D. , Wu Tse‐Chong , Rieke Loretta I. 
Published: November 2003

Abstract

Highly reactive calcium for the preparation of organocalcium reagents: 1‐adamantyl calcium halides and their addition to ketones: 1‐(1‐adamantyl)cyclohexanol

product: 1‐(1‐adamantyl)cyclohexanol

unknown: 1‐octylcyclohexanol

unknown: 1‐(1‐adamantyl)cyclohexanol
(4S)‐(−)‐tert‐Butyldimethylsiloxy‐2‐Cyclopenten‐1‐one
Authors: Paquette Leo A. , Heidelbaugh Todd M. 
Published: November 2003

Abstract

(4S)‐(−)‐tert‐butyldimethylsiloxy‐2‐cyclopenten‐1‐one

reactant: 7.67 g (54 mmol) of (1R,4S)‐(+)‐4‐hydroxy‐2‐cyclopentenyl acetate

intermediate: (1R,4S)‐(−)‐4‐tert‐butyldimethylsiloxy‐2‐cyclopentenyl acetate

product: (4S)‐(−)‐tert‐butyldimethylsiloxy‐2‐cyclopenten‐1‐one
Synthesis of 7‐Substituted Indolines via Directed Lithiation of 1‐(tert‐Butoxycarbonyl)Indoline: 7‐Indolinecarboxaldehyde
Authors: Iwao Masatomo , Kuraishi Tsukasa 
Published: November 2003

Abstract

Synthesis of 7‐substituted indolines via directed lithiation of 1‐(tert‐butoxycarbonyl)indoline: 7‐indolinecarboxaldehyde

intermediate: 1‐(tert‐butoxycarbonyl)indoline

intermediate: 1‐(tert‐butoxycarbonyl)‐7‐indolinecarboxaldehyde

product: 7‐indolinecarboxaldehyde
S‐(−)‐5‐Heptyl‐2‐Pyrrolidinone. Chiral Bicyclic Lactams as Templates for Pyrrolidines and Pyrrolidinones
Authors: Tschantz M. A. , Burgess L. E. , Meyers A. I. 
Published: November 2003

Abstract

S‐(−)‐5‐heptyl‐2‐pyrrolidinone. Chiral bicyclic lactams as templates for pyrrolidines and pyrrolidinones

intermediate: (+)‐3‐Phenyl‐5‐oxo‐7a‐heptyl‐2,3,5,6,7,7a‐hexahydropyrrolo[2,1‐b]oxazole

reactant: 8.56 g of (S)‐(+)‐2‐Phenylglycinol (62.4 mmol)

product: S‐(−)‐5‐Heptyl‐2‐pyrrolidinone

intermediate: 12.4 g of (+)‐N‐[2‐(1‐hydroxy‐2‐phenethyl)]‐5‐heptyl‐2‐pyrrolidinone (40.8 mmol)
An Improved Preparation of 3‐Bromo‐2H‐Pyran‐2‐one: An Ambiphilic Diene for
D
iels‐
A
lder Cycloadditions
Authors: Posner G. H. , Afarinkia K. , Dai H. 
Published: November 2003

Abstract

An Improved preparation of 3‐bromo‐2H‐pyran‐2‐one: An Ambiphilic diene for Diels‐Alder cycloadditions

intermediate: 3‐bromo‐5,6‐dihydro‐2H‐pyran‐2‐one

intermediate: 3,5‐dibromo‐5,6‐dihydro‐2H‐pyran‐2‐one

byproduct: 5‐bromo‐2‐pyrone

product: 3‐bromo‐2‐pyrone

byproduct: 3,5‐dibromo‐2‐pyrone
(−)‐2‐O‐Benzyl‐L‐Glyceraldehyde and Ethyl (R,E)‐4‐O‐Benzyl‐4,5‐Dihydroxy‐2‐Pentenoate
Authors: Steuer B. , Wehner V. , Lieberknecht A. , Jäger V. 
Published: November 2003

Abstract(−)‐2‐O‐benzyl‐L‐Glyceraldehyde and ethyl (R,E)‐4‐O‐benzyl‐4,5‐dihydroxy‐2‐pentenoateintermediate: diethyl (−)‐2,3‐O‐benzylidene‐L‐tartrateintermediate: (+)‐2‐O‐benzyl‐L‐threitolintermediate: (−)‐2‐O‐benzyl‐L‐glyceraldehydereactant: Triethyl phosphonoacetate (22.87 g, 102 mmol)solvent: petroleum ether/ethyl acetateproduct: ethyl (−)‐[R‐(E)]‐4‐O‐benzyl‐4,5‐dihydroxy‐2‐pentenoate
(R)‐(+)‐2‐(Diphenylhydroxymethyl)Pyrrolidine
Authors: Nikolic Nikola A. , Beak Peter 
Published: November 2003

Abstract

(R)‐(+)‐2‐(diphenylhydroxymethyl)pyrrolidine

intermediate: N‐Boc‐pyrrolidine

intermediate: (R)‐(+)‐2‐(diphenylhydroxymethyl)‐N‐(tert‐butoxycarbonyl)pyrrolidine

byproduct: sparteine

product: (R)‐(+)‐2‐(Diphenylhydroxymethyl)pyrrolidine
(S)‐Tetrahydro‐1‐Methyl‐3,3‐Diphenyl‐1H,3H‐Pyrrolo‐[1,2‐
c
][1,3,2]Oxazaborole‐Borane Complex
Authors: Xavier Lyndon C. , Mohan Julie J. , Mathre David J. , Thompson Andrew S. , Carroll James D. , Corley Edward G. , Desmond Richard 
Published: November 2003

Abstract

(S)‐Tetrahydro‐1‐methyl‐3,3‐diphenyl‐1H,3H‐Pyrrolo‐[1,2‐
c
][1,3,2]Oxazaborole‐Borane Complex

intermediate: (S)‐proline‐N‐carboxyanhydride

intermediate: (S)‐diphenylprolinol sulfate

intermediate: (S)‐1,1‐diphenylprolinol

product: (S)‐Tetrahydro‐1‐methyl‐3,3‐diphenyl‐1H,3H‐pyrrolo[1,2‐c][1,3,2]oxazaborole‐borane complex

intermediate: oxazaborolidine

product: (R)‐2,3‐Dihydro‐1H‐inden‐1‐ol

byproduct: 1‐Indanol

product: α,α‐diphenyl‐2‐pyrrolidinemethanol

product: (R)‐ or (S)‐α,α‐diphenyl‐2‐pyrrolidinemethanol
Preparation and Reactions of 2‐tert‐Butyl‐1,1,3,3‐Tetramethylguanidine: 2,2,6‐Trimethylcyclohexen‐1‐yl Iodide
Authors: Barton Derek H. R. , Chen Mi , Jászberényi Joseph Cs. , Taylor Dennis K. 
Published: November 2003

Abstract

Preparation and reactions of 2‐tert‐butyl‐1,1,3,3‐tetramethylguanidine: 2,2,6‐trimethylcyclohexen‐1‐yl iodide

intermediate: 2‐tert‐butyl‐1,1,3,3‐tetramethylguanidine 1

product: 2,2,6‐Trimethylcyclohexen‐1‐yl iodide (2)

reactant: 2,2,6‐trimethylcyclohexanone hydrazone (4.6 g, 0.03 mol)
2,3‐Dibromo‐1‐(Phenylsulfonyl)‐1‐Propene as a Versatile Reagent for the Synthesis of Furans and Cyclopentenones: 2‐Methyl‐4‐[(Phenyl‐Sulfonyl)Methyl]Furan and 2‐Methyl‐3‐[(Phenylsulfonyl)Methyl]‐2‐Cyclopenten‐1‐One
Authors: Watterson Scott H. , Ni Zhijie , Murphree Shaun S. , Padwa Albert 
Published: November 2003

Abstract

2,3‐dibromo‐1‐(phenylsulfonyl)‐1‐propene as a versatile reagent for the synthesis of furans and cyclopentenones: 2‐methyl‐4‐[(phenyl‐sulfonyl)methyl]furan and 2‐methyl‐3‐[(phenylsulfonyl)methyl]‐2‐cyclopenten‐1‐one

intermediate: 1‐(phenylsulfonyl)‐1,2‐propadiene

intermediate: 2,3‐dibromo‐1‐(phenylsulfonyl)‐1‐propene

product: 2‐methyl‐4‐[(phenylsulfonyl)methyl]furan

product: 2‐methyl‐3‐[(phenylsulfonyl)methyl]‐2‐cyclopenten‐1‐one
Cyclopentanone Annulation via Cyclopropanone Derivatives: (3aβ,9bβ)‐1,2,3a,4,5,9b‐Hexahydro‐9b‐Hydroxy‐3a‐Methyl‐3H‐Benz[e]Inden‐3‐One
Authors: Bradlee Michael J. , Helquist Paul 
Published: November 2003

Abstract

Cyclopentanone annulation via cyclopropanone derivatives: (3aβ,9bβ)‐1,2,3a,4,5,9b‐hexahydro‐9b‐hydroxy‐3a‐methyl‐3H‐benz[e]inden‐3‐one

intermediate: 2‐(1‐hydroxycyclopropyl)‐2‐methyl‐1‐tetralone

product: (3aβ,9bβ)‐1,2,3a,4,5,9b‐hexahydro‐9b‐hydroxy‐3a‐methyl‐3H‐benz[e]inden‐3‐one
Nickel‐Catalyzed, Geminal Dimethylation of Allylic Dithioacetals: (E)‐1‐Phenyl‐3,3‐Dimethyl‐1‐Butene
Authors: Yuan Tien‐Min , Luh Tien‐Yau 
Published: November 2003

Abstract

Nickel‐catalyzed, geminal dimethylation of allylic dithioacetals: (E)‐1‐phenyl‐3,3‐dimethyl‐1‐butene

intermediate: (E)‐2‐methyl‐2‐(2‐phenylethenyl)‐1,3‐dithiolane

product: (E)‐1‐phenyl‐3,3‐dimethyl‐1‐butene
Mesitylenesulfonylhydrazine, and (1α,2α,6β)‐2,6‐Dimethylcyclohexanecarbonitrile and (1α,2β,6α)‐2,6‐Dimethylcyclohexanecarbonitrile as a Racemic Mixture
Authors: Reid Jack R. , Dufresne Richard F. , Chapman John J. 
Published: November 2003

Abstract

Mesitylenesulfonylhydrazine, and (1α,2α,6β)‐2,6‐dimethylcyclohexanecarbonitrile and (1α,2β,6α)‐2,6‐dimethylcyclohexanecarbonitrile as a racemic mixture

product: Mesitylenesulfonylhydrazine (1)

intermediate: mesitylenesulfonyl chloride

product: (1α,2α,6β)‐2,6‐Dimethylcyclohexanecarbonitrile and (1α,2β,6α)‐2,6‐Dimethylcyclohexanecarbonitrile (2)

product: 4‐tert‐Butylcyclohexanecarbonitrile

product: 4,4‐Dimethylcyclohexanecarbonitrile

product: 4‐Isopropylcyclohexanecarbonitrile

product: 2,3,3‐Trimethylbutanenitrile

product: 3,4,4‐Trimethylcyclohexanecarbonitrile

product: 3,3,5‐Trimethylcyclohexanecarbonitrile

product: 3‐tert‐Butylcyclopentanecarbonitrile

product: 2,6‐Dimethylcyclohexanecarbonitrile
3‐Chloro‐2‐(Chloromethyl)‐1‐Propene
Authors: Mondanaro Lynch Kathleen , Dailey William P. 
Published: November 2003

Abstract

3‐Chloro‐2‐(chloromethyl)‐1‐propene

intermediate: pentaerythrityl tetrachloride

intermediate: pentaerythrityl trichlorohydrin

product: 3‐Chloro‐2‐(chloromethyl)‐1‐propene

intermediate: Tris(chloromethyl)acetic acid (205 g, 1.00 mol)
[1.1.1]PROPELLANE
Authors: Mondanaro Lynch Kathleen , Dailey William P. 
Published: November 2003

Abstract

[1.1.1]Propellane

intermediate: 1,1‐Dibromo‐2,2‐bis(chloromethyl)cyclopropane

product: [1.1.1]Propellane

product: bicyclo[1.1.1]pentyl phenyl sulfide

product: bicyclo[1.1.1]pentyl sulfide
Synthesis of cis‐4a(S),8a(R)‐Perhydro‐6(2H)‐Isoquinolinones from Quinine: 4a(S), 8a(R)‐2‐Benzoyloctahydro‐6(2H)‐Isoquinolinone
Authors: Hutchison Darrell R. , Khau Vien V. , Martinelli Michael J. , Nayyar Naresh K. , Peterson Barry C. , Sullivan Kevin A. 
Published: November 2003

Abstract

Synthesis of cis‐4a(S),8a(R)‐perhydro‐6(2H)‐isoquinolinones from quinine: 4a(S), 8a(R)‐2‐benzoyloctahydro‐6(2H)‐isoquinolinone

intermediate: Quininone

intermediate: meroquinene tert‐butyl ester

intermediate: benzamide

intermediate: 4a(S),8a(R)‐2‐Benzoyl‐1,3,4,4a,5,8a‐hexahydro‐6(2H)‐isoquinolinone

intermediate: 4a(S),8a(R)‐2‐Benzoyloctahydro‐6(2H)‐isoquinolinone
(1S,2R)‐1‐Aminoindan‐2‐ol
Authors: Larrow Jay F. , Roberts Ed , Verhoeven Thomas R. , Ryan Ken M. , Senanayake Chris H. , Reider Paul J. , Jacobsen Eric N. 
Published: November 2003

Abstract

(1S,2R)‐1‐aminoindan‐2‐ol

intermediate: epoxyindane

intermediate: aminoindanol

intermediate: aminoindanol‐tartrate salt
Asymmetric Synthesis of α‐Amino Acids by the Alkylation of Pseudoephedrine Glycinamide:
L
‐Allylglycine and N‐Boc‐
L
‐Allylglycine
Authors: Myers Andrew G. , Gleason James L. 
Published: November 2003

Abstract

Asymmetric synthesis of α‐amino acids by the alkylation of pseudoephedrine glycinamide:
L
‐allylglycine and N‐Boc‐
L
‐allylglycine

reactant: 60.0 g (0.363 mol, 1 equiv) of (R,R)‐(−)‐pseudoephedrine

reactant: 40.4 g (0.454 mol, 1.25 equiv) of glycine methyl ester

intermediate: (R,R)‐(−)‐pseudoephedrine glycinamide monohydrate

intermediate: (R,R)‐(−)‐pseudoephedrine glycinamide

intermediate: pseudoephedrine L‐allylglycinamide

product: L‐allylglycine

product: N‐Boc‐L‐allylglycine
Ethyl 5‐Chloro‐3‐Phenylindole‐2‐Carboxylate
Authors: Fürstner Alois , Hupperts Achim , Seidel Günter 
Published: November 2003

Abstract

Ethyl 5‐chloro‐3‐phenylindole‐2‐carboxylate

intermediate: N‐(2‐benzoyl‐4‐chlorophenyl)oxalamic acid ethyl ester

product: ethyl 5‐chloro‐3‐phenylindole‐2‐carboxylate
6‐Chloro‐1‐Hexene and 8‐Chloro‐1‐Octene
Authors: Mazerolles Pierre , Boussaguet Paul , Huc Vincent 
Published: November 2003

Abstract

6‐chloro‐1‐hexene and 8‐chloro‐1‐octene

intermediate: Allylmagnesium bromide

reactant: allyl bromide (181.60 g, 1.50 mol)

product: 6‐Chloro‐1‐hexene

reactant: 1‐bromo‐3‐chloropropane (150.00 g, 0.95 mol)

reactant: 1‐bromo‐5‐chloropentane (88.37 g, 0.47 mol)

product: 8‐chloro‐1‐octene
Use of Cerium(III) Chloride in the Reactions of Carbonyl Compounds with Organolithiums or
G
rignard Reagents for the Suppression of Abnormal Reactions:1‐Butyl‐1,2,3,4‐Tetrahydro‐1‐Naphthol
Authors: Takeda Nobuhiro , Imamoto Tsuneo 
Published: November 2003

Abstract

Use ofcerium(III) chloride in the reactions of carbonyl compounds with organolithiums or Grignard reagents for the suppression of abnormal reactions:1‐butyl‐1,2,3,4‐tetrahydro‐1‐naphthol

product: 1‐butyl‐1,2,3,4‐tetrahydro‐1‐naphthol

product: PhCHCHC(OH)(Me)PH

product: Ph(Me)CHCH
2
COPh

product: PhCHCHC(OH)(Me)Ph

product: p‐IC6H4C(OH)(Me)Bu

product: PhCH
2
COCH(Ph)CO2Me

product: PhCH
2
COPr‐i

product: PhCH
2
C(OH)(Pr‐i)2

product: PhCH
2
COCH(Ph)CO2Me

product: PhCH
2
COPr‐i

product: PhCH
2
C(OH)(Pr‐i)2

product: Et3CC(OH)Me2

product: Et3CC(OH)Me2
Copper‐Catalyzed Conjugate Addition of Functionalized Organozinc Reagents to α,β‐Unsaturated Ketones: Ethyl 5‐(3‐Oxocyclohexyl)Pentanoate
Authors: Lipshutz B. H. , Wood M. R. , Tirado R. 
Published: November 2003

Abstract

Copper‐catalyzed conjugate addition of functionalized organozinc reagents to α,β‐unsaturated ketones: ethyl 5‐(3‐oxocyclohexyl)pentanoate

product: Ethyl 5‐(3‐oxocyclohexyl)pentanoate

reactant: 6.7 mL of neat ethyl 5‐iodovalerate (10.24 g, 40.0 mmol)
5‐Phenyldipyrromethane and 5,15‐Diphenylporphyrin
Authors: Boyle Ross W. , Bruckner Christian , Posakony Jeffrey , James Brian R. , Dolphin David 
Published: November 2003

Abstract

5‐phenyldipyrromethane and 5,15‐diphenylporphyrin

product: 5‐phenyldipyrromethane

product: 5,15‐diphenylporphyrin
Preparation of [R‐(R,S)]‐β‐Methyl‐α‐Phenyl‐1‐Pyrrolidineethanol
Authors: Zhao Dalian , Chen Cheng‐yi , Xu Feng , Tan Lushi , Tillyer Richard , Pierce Michael E. , Moore James R. 
Published: November 2003

Abstract

Preparation of [R‐(R,S)]‐β‐methyl‐α‐phenyl‐1‐pyrrolidineethanol

product:
[R‐(R,S)]‐β‐methyl‐α‐phenyl‐1‐pyrrolidineethanol
Synthesis of (S,E)‐1‐(Methoxymethoxy)‐1‐Tributylstannyl‐2‐Butene
Authors: Marshall James A. , Garofalo Albert W. , Hinkle Kevin W. 
Published: November 2003

Abstract

Synthesis of (S,E)‐1‐(methoxymethoxy)‐1‐tributylstannyl‐2‐butene

product: (S,E)‐1‐methoxymethyl)‐1‐tributylstannyl‐2‐butene
Allylindation in Aqueous Media: Methyl 3‐(Hydroxymethyl)‐4‐Methyl‐2‐Methylenepentanoate
Authors: Bennett George D. , Paquette Leo A. 
Published: November 2003

Abstract

Allylindation in aqueous media: methyl 3‐(hydroxymethyl)‐4‐methyl‐2‐methylenepentanoate

reactant:
15.8 g (0.10 mol) of methyl 3‐hydroxy‐4‐methyl‐2‐methylenepentanoate

product:
Methyl 3‐(hydroxymethyl)‐4‐methyl‐2‐methylenepentanoate

intermediate:
11.0 g (0.05 mol) of methyl Z‐2‐(bromomethyl)‐4‐methylpent‐2‐enoate
7α‐Acetoxy‐(1Hβ, 6Hβ)‐Bicyclo[4.4.1]Undeca‐2,4,8‐Triene via Chromium‐Mediated Higher Order Cycloaddition
Authors: Rigby James H. , Fales Kevin R. 
Published: November 2003

Abstract

7α‐acetoxy‐(1Hβ, 6Hβ)‐bicyclo[4.4.1]undeca‐2,4,8‐triene via chromium‐mediated higher order cycloaddition

intermediate: tricarbonyl(η
6
‐cycloheptatriene)chromium(0)

product: ∼98% pure, 7α‐acetoxy‐(1Hβ, 6Hβ)‐bicyclo[4.4.1]undeca‐2,4,8‐triene

reactant: (E)‐1‐acetoxy‐1,3‐butadiene

byproduct: [6π + 2π] cycloadduct
α‐Tosylbenzyl Isocyanide
Authors: Sisko Joseph , Mellinger Mark , Sheldrake Peter W. , Baine Neil H. 
Published: November 2003

Abstract

α‐tosylbenzyl isocyanide

intermediate: p‐toluenesulfinic acid

intermediate: N‐(α‐tosylbenzyl)formamide

product: α‐tosylbenzyl isocyanide
3‐Nitropropanal, 3‐Nitropropanol, and 3‐Nitropropanal Dimethyl Acetal
Authors: Griesser H. , Öhrlein R. , Schwab W. , Ehrler R. , Jäger V. 
Published: November 2003

Abstract

3‐nitropropanal, 3‐nitropropanol, and 3‐nitropropanal dimethyl acetal

product: 3‐Nitropropanal

reactant: 33.4 mL (28.0 g, 0.500 mol) of acrolein

product: 3‐nitropropanol

reactant: 63.7 g (0.600 mol) of trimethyl orthoformate

product: 3‐nitropropanal dimethyl acetal

product: 3‐nitropropanal diethyl acetal
2,4,6‐Trimethylpyrylium Trifluoromethanesulfonate
Authors: Balaban A. T. , Boulton A. J. 
Published: November 2003

Abstract

2,4,6‐Trimethylpyrylium trifluoromethanesulfonate

product: 2,4,6‐trimethylpyrilium trifluoromethane sulfonate
FT‐IR Spectroscopy
Authors: Gregoriou Vasilis G. , Rodman Sheila E. 
Published: November 2003

AbstractFourier transform infrared (FT‐IR) spectroscopy is an ideal analytical technique for the study of condensed phase materials if chemical specificity and selectivity are sought. A complementary technique to raman spectroscopy, FT‐IR has gained widespread acceptance as a characterization tool primarily due to its universality and versatility. The addition of microscopy and imaging to the arsenal of available FT‐IR techniques have increased the popularity and use of FT‐IR even further. Finally, specific examples that illustrate the power of FT‐IR to solve characterization problems are presented here.