Chemistry of Proximal π-Bond Systems. Part I. Synthesis of Vicinal Exocyclic Dimethylene Hydrocarbons

Abstract

Thirteen new bi- or polycyclic vicinal exocyclic dimethylene hydrocarbons (10–22) have been synthesized and some of their spectral properties recorded. The generally most useful synthetic route to such compounds utilizes base-catalyzed double elimination from trans-1,2-bis(hydroxymethyl)alkyl p-toluenesulfonates as the final step in the production of the conjugated diene.