Photosolvolysis of 5-substituted DIBENZOSUBEROL (cas 1210-34-0) derivatives: a stereoelectronic requirements for carbocation photogeneration

Add time:07/20/2019    Source:sciencedirect.com

The possible photosolvolysis of 5-substituted 5H-DIBENZOSUBEROL (cas 1210-34-0)s (3–6) has been studied in aqueous methanol. Only the parent system, 5H-dibenzosuberol (3) reacts via photosolvolysis. On extended photolysis, compounds 3–6 undergo a fragmentation reaction (Φ=0.02–0.08) to give 9,10-dihydrophenanthrene (10) and a carbene-derived product. Evidence gathered from conformational analyses of compounds 3–6 using PCMODEL and MMX, an X-ray crystal structure of 6 and proton nuclear magnetic resonance (1H NMR) studies using a lanthanide shift reagent indicates that only in alcohol 3 is the hydroxyl group of the substrate oriented in a pseudo-axial position, whereas for the compounds 4–6 the hydroxyl group is in a pseudo-equatoial position. It appears that an axial hydroxyl group is a necessary requirement for photosolvolysis in these systems since it allows for correct stereoelectronic alignment of the π orbitals of the benzene rings with the developing empty, pz orbital as the Ar2COH bond dissociates heterolytically.

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