Reaction of essentially free benzyl cations with acetonitrile; synthesis of ethanimidic carboxylic anhydrides and unsymmetrical diacylamines

RW Darbeau, EH White, N Nunez, B Coit…

Index: Darbeau, Ron W.; White, Emil H.; Nunez, Nicholas; Coit, Brian; Daigle, Mark Journal of Organic Chemistry, 2000 , vol. 65, # 4 p. 1115 - 1120

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Citation Number: 24

Abstract

Benzyl cations were generated via the thermal decomposition of N-benzyl-N- nitrosopivalamide in acetonitrile and acetonitrile-water mixtures at 25° C. The first-formed (primary) benzylating agent, the benzyl cation, was scavenged competitively by pivalate (trimethyl acetate) ion to yield benzyl pivalate, by acetonitrile to yield the corresponding N- benzylnitrilium ion, and by water (when present) to yield benzyl alcohol. The nitrilium ion ...