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Regioselectivity in \alpha-Cleavage Reactions: Arylalkylcyclopropenethiones

Singh, Sharat and Ramamurthy, Vaidyanathan (1985) Regioselectivity in \alpha-Cleavage Reactions: Arylalkylcyclopropenethiones. In: Journal of Organic Chemistry, 50 (20). pp. 3732-3738.

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Photoreactions of several arylalkylcyclopropenethiones (1b-e) have been investigated. The products formed have been rationalized on the basis of \alpha-cleavage as the primary photoprocess. The photochemical \alpha-cleavage is presumed to originate from the lowest excited $n\pi^*$ riplet state. A ioselective \alpha-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.

Item Type: Journal Article
Publication: Journal of Organic Chemistry
Publisher: American Chemical Society
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 16 Jul 2008
Last Modified: 19 Sep 2010 04:47
URI: http://eprints.iisc.ac.in/id/eprint/15049

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