Reactions of cyclohexadienes. X. Some dichlorocarbene adducts of alkoxycyclohexa- 1,4-dienes and their conversion into hydroxycyclopropanes and cycloheptenones

Abstract

Some reactions of dichlorocarbene adducts of alkoxycyclohexa-1,4-dienes have been examined. The tetrahydropyranyl ethers lead to dichlorohydroxycyolopropanes, which often undergo ready ring fission to give initially chlorocycloheptenones. Bis-adducts can produce cyclooctane derivatives. β-(2?-Pyranyloxy)-1,4,5,8-tetra- hydronaphthalenes give rise with dichlorocarbene to bis- or tris- adducts in which one cyclopropane ring can be opened through the hydroxycyclopropane to give ring-fused cycloheptenone derivatives.