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Photochemistry of benzylidene-d,l-piperitones in solution and the melt phase

Venugopalan, P and Weiss, Richard G and Venkatesan, K (1992) Photochemistry of benzylidene-d,l-piperitones in solution and the melt phase. In: Journal of Organic Chemistry, 57 (1). pp. 276-279.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo00027a049


The solution- and melt-phase photochemistry of four trans-benzylidene-d,l-piperitones (1) has been investigated under a variety of conditions. The 1 undergo trans reversible cis isomerization to establish a quasi photostationary state. Further irradiation leads to 2 via oxidative ring closure. Conspicuously absent are dimers (obtained upon irradiation of the neat crystals) and the plausible Norrish Type II photoproducts, 3. Although 1c yields 2c, no evidence for the alternative cyclization route to 2a (requiring loss of HCl) has been observed. Rationalizations for the transformations are presented. The structure of 2b has been determined unambiguously from X-ray crystallographic analysis.

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: 02 May 2011 05:25
Last Modified: 02 May 2011 05:25
URI: http://eprints.iisc.ac.in/id/eprint/37304

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