Tetrahedron

The reaction of isoquinolinium N-phenylimide with 1-(diethylamino) propyne and carbon disulfide

R Temme, K Polborn, R Huisgen

Index: Temme, Robert; Polborn, Kurt; Huisgen, Rolf Tetrahedron, 1998 , vol. 54, # 33 p. 9849 - 9858

Full Text: HTML

Citation Number: 5

Abstract

The cycloadduct 1 exists in a mobile equilibrium with isoquinolinium N-phenylimide (2) and CS2. The reaction of 1 with 1-(diethylamino) propyne (3) afforded the 1: 1: 1 products 4 and 5, the latter predominating with higher CS2 concentration. The NMR spectra and an X-ray analysis of 4 clarified the structures. The hindered rotation about the C N bond of the N, N- diethylthiocarboxamide groups is responsible for the temperature-dependent dynamic ...