Divergent oxidative rearrangements in solution and in a zeolite: Distal vs proximal bond cleavage of methylenecyclopropanes

…, M Oshima, HD Roth, S Tero-Kubota…

Index: Ikeda, Hiroshi; Nomura, Tsuyoshi; Akiyama, Kimio; Oshima, Mitsuhiro; Roth, Heinz D.; Tero-Kubota, Shozo; Miyashi, Tsutomu Journal of the American Chemical Society, 2005 , vol. 127, # 41 p. 14497 - 14504

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Citation Number: 15

Abstract

Irradiation of 9, 10-dicyanoanthracene (DCA) or p-chloranil in the presence of E-1- benzylidene-2-phenylcyclopropane (E-5) in CH2Cl2 causes E-5 to undergo methylenecyclopropane rearrangement. An adduct, Z-7, between DCA and 5 firmly supports the involvement of a bifunctional trimethylenemethane radical cation. In contrast, incorporation of E-5 into HZSM-5 produces trans, trans-1, 4-diphenyl-1, 3-butadiene ...