Tetrahedron

Photooxygenation of 3-acetyl-5-aryl-2-methylfurans via endoperoxide intermediate and the following reactions

S Onitsuka, H Nishino, K Kurosawa

Index: Onitsuka, Satoaki; Nishino, Hiroshi; Kurosawa, Kazu Tetrahedron, 2001 , vol. 57, # 28 p. 6003 - 6009

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Citation Number: 16

Abstract

The photooxygenation of 3-acetyl-5-aryl-2-methylfurans 1a–e selectively produced 2, 2- diacetyl-3-aroyloxiranes 2a–e, 3-acetyl-1-aryl-2-pentene-1, 4-diones 3a–e, and 3-acetyl-1- aryl-2-hydroxy-2-pentene-1, 4-diones 4a–d via the endoperoxide intermediate A depending on the reaction conditions and the work-up procedure. The oxiranes 2a–e were mainly obtained in 56–77% yields by allowing the reaction mixture to stand at ambient ...