Diaxial ring opening of 1, 2-oxidocyclohexanes

FG Bordwell, RR Frame, JG Strong

Index: Bordwell,F.G. et al. Journal of Organic Chemistry, 1968 , vol. 33, # 9 p. 3385 - 3388

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Citation Number: 4

Abstract

8 axial opening by attack at C-2 of the conjugate acid of conformation 6a of the epoxide would have re-formed bromohydrin 5. The success of the method depends, therefore, not only on the preference for diaxial ring opening, 2 but also on a preference for reaction via conformation 6b rather than 6a. This latter preference is