The Curtius Rearrangement of Cyclopropyl and Cyclopropenoyl Azides. A Combined Theoretical and Experimental Mechanistic Study

V Tarwade, O Dmitrenko, RD Bach…

Index: Tarwade, Vinod; Dmitrenko, Olga; Bach, Robert D.; Fox, Joseph M. Journal of Organic Chemistry, 2008 , vol. 73, # 21 p. 8189 - 8197

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Citation Number: 14

Abstract

A combined experimental and theoretical study addresses the concertedness of the thermal Curtius rearrangement. The kinetics of the Curtius rearrangements of methyl 1- azidocarbonyl cycloprop-2-ene-1-carboxylate and methyl 1-azidocarbonyl cyclopropane-1- carboxylate were studied by 1H NMR spectroscopy, and there is close agreement between calculated and experimental enthalpies and entropies of activation. Density functional ...