Add time:09/24/2019         Source:sciencedirect.com

The synthesis and photochemistry of 4,4-diphenyl-2-cyclohepten-1-one are reported. Despite the presence of phenyls at C-4, irradiation of the title compound affords only the [2+2] cycloaddition products; no phenyl-migration products normally associated with 4,4-diphenyl-2-cyclohexe-1-one photochemistry are observed. The structure and stereochemistry of the products have been unequivocally assigned by X-ray crystallographic methods as the trans-syn-trans (major) and the trans-anti-trans head-to-head dimers. The ratio of the products (2.4:1) is the same in tert-butyl alcohol and benzene. The current work provides the first definitive structural assignments for photochemically-derived cycloheptenone dimers. The mechanism can be rationalized in terms of a ground state asynchronous [π2s + π2a] cycloaddition or a stepwise diradical-mediated addition of the intermediate trans-2-cycloheptenone species to a molecule of the cis enone.

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