Add time:07/12/2019         Source:sciencedirect.com

The photochemistry of (±)-3,4,4a,5,6,7-hexahydro-4a-methyl-7,7-diphenyl-1(2H)-naphthalenone (1) and (±)-3,4,4a,5,6,7-hexahydro-4a-7,7-trimethyl-1(2H)-napthalenone (2) is presented. Both molecules incorporate a rigid s-cis enone extended over two rings. In benzene, substrates 1 and 2 were photoinert. In alcohol solvents, hydrogen-bonded enols resulting from solvent addition to the enone doubel bond were isolated as the only photoproducts. The rearrangements anticipated for γ,γ-disubstituted enones, aryl migration for 1 and Type A rearrangement for 2, were not observed. Spectroscopic and X-ray structure elucidation showed that solvent addition is highly regio- and stereospecific. Ketonization of the less hindered enols derived from 2 was observed upon heating or exposure to silica gel; enols produced from 1 were stable. Photolysis of 1 and 2 in aqueous dioxane led exclusively to β-hydroxy ketones. The mechanism leading to product formation was rationalized in terms of a stepwise addition of solvent to a triplet-derived ground state trans enone. A mechanism involving direct addition of solvent to a polarized excited state was also considered.

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