Regioselectivity in α-cleavage reactions

Arylalkylcyclopropenethiones

Research output: Contribution to journalArticle

14 Citations (Scopus)

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
Pages (from-to)3732-3738
Number of pages7
JournalJournal of Organic Chemistry
Volume50
Issue number20
StatePublished - Dec 1 1985
Externally publishedYes

Fingerprint

Regioselectivity
Photolysis
Interfacial energy
Excited states
Ground state
carbene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Regioselectivity in α-cleavage reactions : Arylalkylcyclopropenethiones. / Singh, Sharat; Ramamurthy, Vaidhyanathan.

In: Journal of Organic Chemistry, Vol. 50, No. 20, 01.12.1985, p. 3732-3738.

Research output: Contribution to journalArticle

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