Aryl azide-allene cycloaddition. The contrasting behavior of two simple allenes, 1, 2-cyclononadiene and 1, 2-propadiene

DK Wedegaertner, RK Kattak, I Harrison…

Index: Wedegaertner, Donald K.; Kattak, Rangin K.; Harrison, Isom; Cristie, Sharon K. Journal of Organic Chemistry, 1991 , vol. 56, # 14 p. 4463 - 4467

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Citation Number: 13

Abstract

1, 2-Cyclononadiene (1) reads with phenyl azide (2a) and rl-bromophenyl azide (2b) to give conjugated triezoline adducts 3a and 3b, respectively.(R)-(+)-l and 2a react to give (S)-(+)- 3a, which is consistent with a concerted cycloaddition mechanism. The reaction of 1, 2- propadiene (6) and 2a gives triazoles 8 and 10 plus compound 18 in nearly equal amounts. The formation of these produds is rationalized by a scheme involving initial formation of ...