Abstract
The cycloadduct 1 exists in a mobile equilibrium with isoquinolinium N-phenylimide ( 2) and CS 2. The reaction of 1 with 1-(diethylamino)propyne ( 3) afforded the 1:1:1 products 4 and 5, the latter predominating with higher CS 2 concentration. The NMR spectra and an X-ray analysis of 4 clarified the structures. The hindered rotation about the CN bond of the N, N-diethylthiocarboxamide groups is responsible for the temperature-dependent dynamic processes observed in the 1H NMR spectra of 4 and 5. In analogy with the known reaction of the ynamine 3 with CO 2, the thiocarbamoyl-thioketene 11 is assumed as key intermediate which accepts the 1,3-dipole either at the CC or the CS bond. The reaction of ynamine 3 with CS 2 in the absence of 2 provided a 2:2 product in modest yield.
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