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

Hankinson, Barry ; Heaney, Harry ; Price, Anthony P. ; Sharma, Ram Prakash (1973) Aryne chemistry. Part XXXII. Reactions of tetrahalogenobenzynes with 6,6-dialkylfulvenes, and the photoisomerisation and thermal reactions of derived products Journal of the Chemical Society, Perkin Transactions 1 . pp. 2569-2575. ISSN 0300-922X

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1973...

Related URL: http://dx.doi.org/10.1039/P19730002569

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.

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