Tetrahedron letters

Bergman cycloaromatization of imidazole-fused enediynes: the remarkable effect of N-aryl substitution

Z Zhao, Y Peng, NK Dalley, JF Cannon, MA Peterson

Index: Zhao, Zhengrong; Peng, Yunshan; Dalley, N. Kent; Cannon, John F.; Peterson, Matt A. Tetrahedron Letters, 2004 , vol. 45, # 18 p. 3621 - 3624

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Citation Number: 15

Abstract

A series of N-aryl substitutedimidazole-fused'(Z) 3-ene-1, 5-diynes was prepared and kinetic parameters for their Bergman cycloaromatization reactivities were determined. N-Arylation enhanced rates relative to N-alkyl derivatives by up to sevenfold (ANOVA p< 0.0001). The greatest enhancement was exhibited by the N-phenyl derivative (sevenfold at 145° C).