Allene/haloolefin electrocyclic reactions: a new route to stable triarylmethyl radicals

…, DJ Hogenkamp, FF Khouri

Index: Porter, Ned A.; Hogenkamp, Derk J.; Khouri, Farid F. Journal of the American Chemical Society, 1990 , vol. 112, # 6 p. 2402 - 2407

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Citation Number: 15

Abstract

Abstract: Electrocyclization of allene I, l-diphenyl-3-[2-(2-bromoethenyl) phenyl] propadiene (5), followed by one-electron reduction with elemental mercury, gives P- naphthyldiphenylmethyl radical 6 in good yield. In the absence of mercury, the only product isolated is the corresponding triarylmethyl halide. Although both reactions presumably involve an intermediate o-quinodimethane species, no evidence for this intermediate was ...