Surface photochemistry: silica gel as a medium for photochemical cycloaddition of enones to aliene

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Abstract
The photocycloaddition of allene to the steroidal enone 1a, normally occurring from the (less hindered) α side, has been directed in part to the (more hindered) β side by adsorption on the surface of silica gel. For a series of cyclic enone–allene photocycloadditions it is shown that the normally favored formation of the β,γ-regioisomeric adduct in homogeneous systems can be shifted to favor the γ,δ adduct on a silica gel surface.

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