Addition of dichlorocarbene to some acyclic trienes

Abstract

The preparation of dichlorocarbene adducts of the following olefins is described: cis- and trans-deca-1,5,9-triene deca-1,trans-4,9-triene, octa-1, trans-3,cis-6-triene, octa-1,trans-3,7-triene, and 5-methylhepta-1,trans-3,6-triene. The relative reactivities of the double bonds towards dichlorocarbene were in the order, conjugated vinyl > conjugated internal > cis > trans > vinyl. The effect of base on some of the olefins is discussed.