Base-Induced Photocyclization of 1,2-Diaryl-1-tosylethenes. A Mechanistically Novel Approach to Phenanthrenes and Phenanthrenoids
Organic Letters2003Vol. 5(26), pp. 4939–4941
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Abstract
The irradiation with UV light of a number of 1,2-diaryl-1-tosylstilbenes, in the presence of base, leads to the corresponding phenanthrenes and heterocyclic analogues. These results are consistent with a mechanism involving the base-induced elimination of p-toluenesulfinic acid from an intermediate 9-tosyl-4a,4b-dihydrophenanthrene, formed by photochemical cyclization of the starting 1,2-diaryl-1-tosylstilbenes. [reaction: see text]
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