Journal of the American Chemical Society

Electrocyclic ring opening of a. beta.-lithiocyclopropyloxirane. Generation and trapping of (2Z, 4E)-cyclohepta-2, 4-dienol

RM Coates, LA Last

Index: Coates, Robert M.; Last, Larry A. Journal of the American Chemical Society, 1983 , vol. 105, # 25 p. 7322 - 7326

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Citation Number: 8

Abstract

Abstract: A novel concerted electrocyclic ring opening of a jMithiocyclopropyloxirane is described. Metalation of exo-7-bromobicyclo [4.1. O] hept-2-ene anti-oxide (3) with n- butyllithium at 0 OC afforded exo-bicyclo [3.2. 0] hept-6-en-2-ol (4). A mechanism involving conrotatory ring opening of the metalated cyclopropane (6) to (Z, E)-cycloheptadiene oxide 7 followed by conrotatory ring closure is proposed to explain the formation of 4. Evidence for ...