Quantitative α-Alkylation of Primary Nitriles

A synthetic pathway that produces alkyl α,ω-cyanodiolefins in quantitative yield is described, applying chemistry that is based on simple α-alkylation of alkyl nitriles. Three amide bases, lithium 2,2,6,6-tetramethylpiperidide, lithium diisopropylamide, and sodium amide, are used to create the α-car...

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Bibliographic Details
Published inSynthetic communications Vol. 37; no. 22; pp. 3923 - 3931
Main Authors Rojas, Giovanni, Baughman, Travis W., Wagener, Kenneth B.
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis Group 01.11.2007
Taylor & Francis
Subjects
Chemistry
Chemistry, Organic
isomerization
LDA
nitriles
Physical Sciences
Science & Technology
terminal olefin
α-Alkylation
nitriles
terminal olefin
REDUCTION
isomerization
alpha-alkylation
ADMET POLYMERIZATION
CONSTRUCTION
DECYANATION
LDA
CYCLIC NITRILES
METATHESIS
POLYETHYLENE
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Summary:A synthetic pathway that produces alkyl α,ω-cyanodiolefins in quantitative yield is described, applying chemistry that is based on simple α-alkylation of alkyl nitriles. Three amide bases, lithium 2,2,6,6-tetramethylpiperidide, lithium diisopropylamide, and sodium amide, are used to create the α-carbanions that undergo substitution with various alkylating agents. Optimization leads to essentially quantitative conversions for every substrate/example reported herein, which will prove useful in many synthetic schemes.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910701572456