The Journal of Organic Chemistry

Requisite cation complexation for the reduction of 2, 6-pyrido-18-crown-6 N-oxide and an analog by potassium tri-sec-butylborohydride. Evidence for a single electron …

WR Wagner, WH Rastetter

Index: Wagner, William R.; Rastetter, William H. Journal of Organic Chemistry, 1983 , vol. 48, # 3 p. 294 - 298

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Citation Number: 6

Abstract

The reductions of 2, 6-pyrido-18-crown-6 N-oxide (1) and a weakly complexing analogue (3) by potassium tri-sec-butylborohydride (K-Selectride) were studied. N-Oxides 1 and 3 are reduced to pyridines 2 and 4, respectively, at equal rates with the reactions obeying competitive, consecutive second-order kinetics with kz/kl= m, In a competitive reduction with limiting K-Selectride, only crown ether 1 is reduced while analogue 3 remains unreacted. ...