An Unexpected Paternò-B chi Reaction in the Crystalline State

T Kang, JR Scheffer

Index: Kang, Ting; Scheffer, John R. Organic Letters, 2001 , vol. 3, # 21 p. 3361 - 3364

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Citation Number: 8

Abstract

The solution and solid-state photochemistry of a series of aryl 1-phenylcyclopentyl ketones (1) was investigated. While typical Norrish type I products were formed in solution, irradiation of crystals of 1 afforded the novel oxetanes 3 and 4 regiospecifically. The formation of the oxetanes is believed to occur through Norrish type I cleavage and hydrogen abstraction, producing an alkene and an aldehyde, followed by a Paternò-Büchi reaction within the ...