Canadian Journal of Chemistry

On the origin of regioselectivity in the photorearrangement of 4, 4-diphenyl-2, 5-cyclohexadiene systems. Synthesis and photochemistry of 4, 4-diphenyl-γ-thiopyran …

D Gravel, C Leboeuf

Index: Gravel, Denis; Leboeuf, Christian Canadian Journal of Chemistry, 1982 , vol. 60, p. 574 - 587

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Citation Number: 19

Abstract

The synthesis from diphenylmethane of 4, 4-diphenyl-γ-thiopyran and 4, 4-diphenyl-γ- thiopyran-1, 1-dioxide is described. Upon direct photolysis at 254 nm the γ-thiopyran derivative undergoes rearrangement to a mixture of 5, 6-diphenyl-2-thiabicyclo-[3.1. 0] hexene and 2, 4-diphenyl-α-thiopyran. The corresponding 1, 1-dioxide derivative on the other hand undergoes, upon direct photolysis at 254 nm or sensitized (acetone) photolysis ...