Photochemical and acid-catalyzed rearrangements of 4-carbomethoxy-4-methyl-3-(trimethylsilyl)-2, 5-cyclohexadien-1-one
AG Schultz, EG Antoulinakis
Index: Schultz, Arthur G.; Antoulinakis, Evan G. Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4555 - 4559
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Citation Number: 28
Abstract
The synthesis of 4-carbomethoxy-4-methyl-3-(trimethylsilyl)-2, 5-cyclohexadien-1-one (1) in 60% overall yield from benzaldehyde is described. Irradiation (366 nm) of 1 in benzene solution gave products of type A photorearrangement; eg, diastereomers of the 4- (trimethylsilyl)-and 5-(trimethylsilyl) bicyclo [3.1. 0] hex-3-en-2-ones 8 and 9. Bicyclohexenones 9a and 9b could not be isolated, but underwent acid-catalyzed ...
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