Quantitative α??Alkylation of Primary Nitriles

G Rojas, TW Baughman, KB Wagener

Index: Rojas, Giovanni; Baughman, Travis W.; Wagener, Kenneth B. Synthetic Communications, 2007 , vol. 37, # 22 p. 3923 - 3931

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Citation Number: 17

Abstract

Abstract 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/ ...