An investigation of the reaction of dehydrogenating agents with a stable 8-Oxatricyclo[4,3,0,0^7,9]nona-2,4-diene and related Bicylo[4,2,0]octa-2,4-dienes as a potential route to isobenzofurans

Abstract

Reaction of the 7,8-dichlorobicyclo[4,2,0]octa-2,4-diene (9) with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone yields the benzocyclobutene (10). Extension of this technique to the related bicyclo[4,2,0]octa-2,4,7-trienes (21) and (23), or 8-oxatricyclo[4,3,0,0^7,9]nona-2,4-diene (6) was unsuccessful. Manganese dioxide was equally unrewarding while o-chloranil reacted with these olefins to yield benzodioxins in a [4+2] cycloaddition reaction.