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Synthetic Communications

Quantitative α??Alkylation of Primary Nitriles

G Rojas, TW Baughman, KB Wagener

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

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被引用次数: 17

摘要

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/ ...