Regioselectivity in α-Cleavage Reactions: Arylalkylcyclopropenethiones

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Abstract

Photoreactions of several arylalkylcyclopropenethiones (1b-e) have been investigated. The products formed have been rationalized on the basis of α-cleavage as the primary photoprocess. The photochemical α-cleavage is presumed to originate from the lowest excited nπ* triplet state. A regioselective α-cleavage reaction has been observed and this unusual regioselectivity is explained on the basis of close approach of the ground-state energy surface of the diradical/carbene, the primary intermediates, to the excited triplet-state surface of cyclopropenethiones. Reactions originating from both triplet and singlet thioketene carbene have been observed upon photolysis of arylalkylcyclopropenethiones.

Original languageEnglish (US)
Pages (from-to)3732-3738
Number of pages7
JournalJournal of Organic Chemistry
Volume50
Issue number20
DOIs
StatePublished - Oct 1985
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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