Photochemical transformations. XXII. Photoisomerization of substituted acrylic acids and acrylamides to. beta.-lactones and. beta.-lactams

OL Chapman, WR Adams

Index: Chapman,O.L.; Adams,W.R. Journal of the American Chemical Society, 1968 , vol. 90, # 9 p. 2333 - 2342

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Citation Number: 64

Abstract

Abstract: Irradiation of cis-a-phenylcinnarnic acid in the presence of tetramethylethylene in degassed ether gives trans-l, 2-diphenyl-3, 3, 4, 4-tetrarnethylcyclobutane. The mechanistic path of the reaction is shown to involve initial isomerization of cis-a-phenylcinnarnic acid to the trans-and cis-p-lactones. The cis-@-lactone is isolated in 79 yield. Irradiation of the cis- @-lactone in the presence of tetramethylethylene gives trans-l, 2-diphenyl-3, 3, 4, 4- ...

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