Tetrahedron

The reactivity of 2-vinylindoles with dimethyl acetylenedicarboxylate

RA Jones, PM Fresneda, TA Saliente, JS Arques

Index: Jones, R. Alan; Fresneda, Pilar Martinez; Saliente, Teresa Aznar; Arques, Jose Sepulveda Tetrahedron, 1984 , vol. 40, # 23 p. 4837 - 4842

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Citation Number: 17

Abstract

The overall rates of reaction of 1-substltuted-1-(1-methyl-2-indolyl) ethenes with dimethyl acetylenedicarboxylate are considerably lower than those of the corresponding 2-vinyl- pyrroles. Steric interaction between the N-methyl group on the indole ring and the 1- substituent on the ethenyl group prevents the diene system adopting a coplanar cisoid configuration and, thereby, inhibits the π4+ π2 cycloaddition reaction of the system with ...