The photochemistry of 1-cyclohexenyl-2,4,6-trimethylphenyl-methanone (1-mesitoyl-cyclohexene)

Add time:07/19/2019    Source:sciencedirect.com

The photochemistry (direct irradiation in solution, λ>300nm) of the title compound (8) has been investigated. Whereas, in contrast to the methyl-free analog of 8, only undefined material of higher molecular weight was obtained upon irradiation without additives in acetonitrile and toluene, this situation changed dramatically in the presence of co-reactants. Thus, in ethyl vinyl ether, [4+2] adducts 11a and 11b were obtained in good combined yield. In acetonitrile, in the presence of acid which catalyses a skeletal rearrangement, the hexahydrofluorenone 14 was the main product. The results point to the intermediacy of the trans-cyclohexene isomer of 8, viz. 9, and to the 2-oxyallyl 10 as consecutive intermediates, in analogy to the methyl-free system. The molecular structures of some unprecedented minor by-products such as 15a–c even more clearly reveal their origin from 10. Photoreactions of 8 in the presence of either water or phenol as co-reactants proceeded less cleanly but did give defined products such as 16–18 in moderate yields.

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