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Photochemistry of .alpha.,.beta.-unsaturated thiones: addition to electron-rich olefins from T1

Rao, Pushkara V and Ramamurthy, V (1988) Photochemistry of .alpha.,.beta.-unsaturated thiones: addition to electron-rich olefins from T1. In: Journal of Organic Chemistry, 53 (2). pp. 327-332.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo00237a020


1,1,3-Trimethyl-2-thioxo-1,2-dihydronaphthale(1n)e adds to electron-rich olefins upon excitation to either Sz (PP*) or Sl (ns*) states. Excitation to S2 level resulted in the same mixture of products, namely thietane and 1,4-dithiane, as on excitation to S1 level. Addition occurs to the thiocarbonyl function and not to the carbon-carbon double bond. The addition is site-specific, and the formation of thietane is regiospecific. The ratio of thietane to 1,4-dithiane in the product mixture is dependent on the concentration of the thioenone. The addition is suggested to originate from the lowest triplet state (Tl) and involves diradical intermediates.

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: 25 Sep 2010 06:55
Last Modified: 25 Sep 2010 06:55
URI: http://eprints.iisc.ac.in/id/eprint/32449

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