ISSN:
1042-7163
Keywords:
Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Perfluoro-2-methyl-2-pentene-thiocyanate-3 reacts with ammonia to give 2,4-diaminoperfluoro-4-methyl-2-pentenethiocyanate-3 (4) and 2-aminoperfluoro-4, 4-dimethyl-4,5-dihydro-5-ethylidene-1,3-thiazole (5). Compound 4 is kinetically stable and at 150°C under-goes rotational isomerization to afford the cyclic isomer 2-amino-4,4-bis(trifluoromethyl)-4,5-dihydro-5-(1-aminoperfluoroethylidene) -1,3-thiazole (6). Intramolecular cyclizations, resulting in the thiazolines 5 and 6, proceed likewise via the Thorpe reaction. For compounds 4-6, X-ray diffraction analyses were undertaken and IR spectra in solution and in solid state were investigated. It is supposed that a high kinetic preference for formation of 4 and the fact that it does not undergo spontaneous cyclization in ammonolysis stem from the NH … N intramolecular hydrogen bonding between two amino groups.
Additional Material:
7 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hc.520030205
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