Triggering of the Bergman Cyclization by Photochemical Ring Contraction. Facile Cycloaromatization of Benzannulated Cyclodeca-3,7-diene-1,5-diynes
- 13 March 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 129 (13) , 3792-3793
- https://doi.org/10.1021/ja064470q
Abstract
Eleven-membered ring enediyne 1, which incorporates an α-diazo-β-diketone moiety, undergoes efficient light-induced ring contraction to produce two isomeric ten-membered ring enediyne compounds. The latter undergo spontaneous facile Bergman cyclization at or below room temperature. In the photochemical or thermal Wolff rearrangement of 1, the alkyl substituent migrates ca. 2 times faster than the alkynyl group.Keywords
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