Tetra-alkylammonium cyanides as nucleophilic and basic reagents

Abstract

The title compounds catalyse the dimerization and polymerization of activated olefins, the Michael reaction, and other base-catalysed reactions. The mechanism of these reactions is discussed in relation to that of the similar tertiary-phosphine-catalysed reactions. Nucleophilic behaviour is inferred in the dimerization and polymerization reactions, and basic behaviour in olefin isomerization. Under comparable conditions the title compounds are more powerful nucleophiles (towards alkyl halides) than sodium cyanide.