Tetrahedron letters

Kinetics and mechanism of the 1, 3-dipolar cycloaddition of phenyl azides to methyl 3-pyrrolidinoacrylate

BH Al-Sader, M Kadri

Index: Al-Sader, Basil H.; Kadri, Mohamed Tetrahedron Letters, 1985 , vol. 26, # 38 p. 4661 - 4664

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Citation Number: 8

Abstract

Abstract Kinetics of cycloadditions of phenyl azides to methyl 3-pyrrolidinoacrylate (2) produced Hammett ϱ= 2.2. An E a of 13.5 kcal mole− 1 and Δ S* of− 37.4 cal. K− l mole− 1 were calculated for the cycloaddition of pO 2 NC 6 H 4 N 3 to 2. The cycloadditions are concerted, non-synchronous, and are controlled by LUMO (azide)-HOMO (dipolarophile) interactions.