Journal of Organic Chemistry

Solution photochemistry. X. Effects of double-bond geometry and of increasing double-bond separation on the photochemical reactions of acyclic nonconjugated …

JR Scheffer, RA Wostradowski

Index: Scheffer,J.R.; Wostradowski,R.A. Journal of Organic Chemistry, 1972 , vol. 37, # 26 p. 4317 - 4324

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Citation Number: 33

Abstract

The triplet-sensitized photochemical reactions of the geometric isomers of the homologous dienes 2a-c, 3a-c, 5a-c, and 6a-c have been investigated. In the case of the 1, s dienes 2a-c, irradiation using acetone as the triplet energy sensitizer leads to cis, trans isomerization and, at a similar rate, to internal “crossed”[2+ 21 cycloaddition to give adducts 7 and 8 in a ratio of 65: 35. Similar excitation of the 1, 6 dienes 3a-c causes concurrent geometric isomerism ...