Degenerate. beta.-aryl rearrangements in photochemically generated triarylvinyl cations

T Kitamura, S Kobayashi, H Taniguchi…

Index: Kitamura, Tsugio; Kobayashi, Shinjiro; Taniguchi, Hiroshi; Fiakpui, Charles Y.; Lee, Choi Chuck; Rappoport, Zvi Journal of Organic Chemistry, 1984 , vol. 49, # 17 p. 3167 - 3170

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Citation Number: 20

Abstract

Irradiation of triphenyl-(la), tri-p-tolyl-(lb), or tri-p-anisylvinyl bromide (lo) in methanol gave the vinyl ethers 4 and the phenanthrenes 5. A study of [2-13C]-labeled bromides showed that@-aryl rearrangement takes place in the photochemically generated vinyl cations 3*. Irradiation of triaryl [2-13C] vinyl bromides I* in trifluoroethanol and analpie of the extent of scrambling from C-2 to C-1 in the trifluoroethyl vinyl ethers 8 showed 38%, 72%, and 92% ...