Journal of the American Chemical Society

Cyclization of 3-diazoalkenes to pyrazoles

JL Brewbaker, H Hart

Index: Brewbaker,J.L.; Hart,H. Journal of the American Chemical Society, 1969 , vol. 91, # 3 p. 711 - 715

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Citation Number: 59

Abstract

Abstract: Eight 3-diazoalkenes have been prepared from the related ethyl alkenylnitrosocarbamates and methanolic sodium methoxide. All of these unsaturated diazo compounds spontaneously cyclized at room temperature to form pyrazoles in essentially quantitative yields. The cyclizations were cleanly unimolecular. The first-order rate constants for the reactions of four substituted trans-3-diazo-1-phenylpropenes fit the Hammett ...

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