Indanyl cations. Stereoselective formation from acyclic phenyl-substituted allylic cations and temperature-dependent rearrangements

CU Pittman, WG Miller

Index: Pittman,C.U.; Miller,W.G. Journal of the American Chemical Society, 1973 , vol. 95, # 9 p. 2947 - 2956

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Citation Number: 39

Abstract

Abstract: The 1, 3-diphenylbutenyl cation (2a) and the 1, 1, 3-tripheny1-2-propenyl cation (2b) have been directly observed by nmr spectroscopy after their generation from their respective allylic alcohols [la and lb) in FSOIH at-70”. These are the first acyclic, phenyl- substituted, allylic cations to be reported. On warming the acid solutions, cyclization to indanyl cations was observed. A series of 12 phenyl-substituted allylic alcohols was ...