The photodecomposition of several sulfonic esters of α‐hydroxymethylbenzion (1a) was studied by means of ESR and 1H NMR‐CIDNP techniques. An exclusive α‐cleavage into benzoyl and α‐hydroxy‐α‐sulfonyloxymethylbenzyl radicals (6 and 7) through a triplet excited state was observed. Radicals (7) were found to undergo elimination of sulfonic acid to give benzoylmethyl radicals (9) in an extremely fast process. Chemical confirmation was provided by naphthalene quenching and radical‐trapping experiments using 1‐dodecanethiol and 2,2,6,6‐tetramethylpiperidin‐1‐oxyl, respectively. Photodecomposition of the sulfonic esters in the presence of 1,1‐diphenylethylene as a model substrate for vinyl monomers indicated that both benzoyl and benzoylmethyl radicals are highly reactive towards the carbon‐carbon double bond.
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