Synthesis and Transformations of Aryl-Substituted Alkenes of the Adamantane Series

Abstract

Aryl-substituted alkenes of the adamantane series, 1-[(Z,E)-3-phenylprop-2-en-1-yl]adamantane and 1-[(Z)-3-phenylprop-1-en-1-yl]adamantane, have been synthesized by the Wittig reaction. Their allylic bromination involves two concurrent reactions, radical substitution and raical addition. The different chemical behaviors of the aryl-substituted alkenes have been demonstrated in the Ritter reaction. Depending on the alkene structure and acid catalyst nature, the products are secondary amides, sulfonic acid derivatives, and homoadamantane γ-sultone.