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

✍ Scribed by Robert Temme; Kurt Polborn; Rolf Huisgen

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 549 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00538-9

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✦ Synopsis

The cyeloadduct 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 $, 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 C-N 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 ynumine 3 with CO2, the thiocarbamoyl-thioketene 11 is assumed as key intermediate which accepts the 1,3-dipole either at the C=C or the C=S 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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