Homolytic versus heterolytic cleavage for the photochemistry of 1-naphthylmethyl derivatives

Abstract
The photochemical cleavage of the 1-naphthylmethyl derivatives, 1–7, has been examined in methanol solvent under both direct and sensitized conditions. The competitition between homolytic and heterolytic cleavage as a function of multiplicity and leaving group has been studied in detail. Only substrates 1, 2, 3, and 7 react on sensitization with xanthone but evidence is presented that the resulting reactivity of 1, 2, and 3 may not be triplet energy transfer but rather exciplex formation. A semi-quantitative scale for photofugacities of the leaving groups from the excited singlet states has been established.

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