Photochemistry of substituted benzyl acetates and benzyl pivalates: a reinvestigation of substituent effects

JW Hilborn, E MacKnight, JA Pincock…

Index: Hilborn; MacKnight; Pincock; Wedge Journal of the American Chemical Society, 1994 , vol. 116, # 8 p. 3337 - 3346

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Citation Number: 73

Abstract

Abstract: The photosolvolysis reactions, in methanol, of six substituted benzyl acetates (7a-9 and benzyl pivalates@ a-9 were studied. Five major benzylic products were formed from two critical intermediates. The ethers (9) were formed from the ion pair, 15, and all of the other products (10-f4) were formed from the radical pair, 16. Quenching studies showed that only excited singlet state reactivity was important. The product yields were found to be highly ...