Mechanistic and exploratory organic photochemistry. LXXXVIII. Stereochemistry at the methane carbon in the di-. pi.-methane rearrangement

HE Zimmerman, JD Robbins…

Index: Zimmerman,H.E. et al. Journal of the American Chemical Society, 1974 , vol. 96, # 14 p. 4630 - 4643

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Abstract

Abstract: 3-Ethyl-3, 5-dimethyl-l, l-diphenyl-l, 4-hexadiene was shown to undergo the di-7r- methane rearrangement. Both cis and trans stereoisomers of 3-ethyl-3-methyl-2-(2'- methylpropenyl)-l, I-diphenylcyclopropane were obtained as photoproducts. This system was used to investigate the stereochemistry of the di-7r-methane rearrangement, since the methane carbon is asymmetric. Also both cis-and rrans-vinylcyclopropane photoproducts ...