Aryne chemistry. Part XXXII. Reactions of tetrahalogenobenzynes with 6,6-dialkylfulvenes, and the photoisomerisation and thermal reactions of derived products

Abstract

Reactions of tetrahalogenobenzynes with 6,6-dialkylfulvenes gave the expected 1,4-dihydro-1,4-methanonaphthalenes. Isomerisation of the strained double bond occurred during the catalytic hydrogenation of 5,6,7,8-tetrafluoro-1,4-dihydro-9-isopropylidene-1,4-methanonaphthalene (1). Mass spectra of compound (1) and analogues are reported. The high temperature reactions of a number of dihydro analogues of compound (1) resulted mainly in isomerisations to derivatives of cyclopentindene, and the di-π-methane photoisomerisation of compound (1) occurred in high yield in solution in acetone.