Abstract
[reaction: see text] Photolysis of alpha-keto amides bearing 4-YC(6)H(4)O leaving groups at the position alpha to the keto group efficiently produces high yields of phenols when Y is an electron-withdrawing group or H. The photoelimination likely involves cleavage of zwitterionic intermediates produced via excited-state hydrogen transfer. When Y is an electron-donating group, competing excited-state ArO-C(alpha) bond scission to radicals occurs, followed by recombination to give 1,3-photorearrangment products.
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