Mechanism of photosolvolytic rearrangement of p-hydroxyphenacyl esters: evidence for excited-state intramolecular proton transfer as the primary photochemical step

…, JET Corrie, VRN Munasinghe, P Wan

Index: Zhang, Kai; Corrie, John E. T.; Munasinghe, V. Ranjit N.; Wan, Peter Journal of the American Chemical Society, 1999 , vol. 121, # 24 p. 5625 - 5632

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Citation Number: 83

Abstract

The photosolvolytic rearrangement of a variety of p-hydroxyphenacyl esters and related compounds 7-16 has been studied in solutions with up to 50% aqueous content, using product studies, triplet quenchers, and nanosecond laser flash photolysis. The p- hydroxyphenacyl moiety has recently been proposed as a new and efficient photoactivated protecting group in aqueous solution. Practical applications have been demonstrated, but ...