Mechanistic and exploratory organic photochemistry. XLI. Di-. pi.-methane rearrangement. Interaction of electronically excited vinyl chromophores

HE Zimmerman, PS Mariano

Index: Zimmerman,H.E.; Mariano,P.S. Journal of the American Chemical Society, 1969 , vol. 91, # 7 p. 1718 - 1727

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Citation Number: 81

Abstract

Abstract: The divinyl version of the di-x-methane rearrangement described by us earlier was extended to an acyclic system in order to elucidate the nature of the rearrangement as a function of structure. Thus, 1, 1, 5, 5-tetraphenyl-3, 3-dimethyl-l, Cpentadiene (5) was synthesized; on direct irradiation 5 afforded 1, l-diphenyl-2, 2-dimethyl-3-(2, 2-diphenylvinyl) cyclopropane (8) as the sole primary photoproduct. Isotope dilution analysis was ...