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Acylgruppenwanderung in N-Acyl-2H-imidazol-4(3H)-thionen |
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| Authors: | Prof Dr F Asinger A Saus E Fichtner W Leuchtenberger |
| Institution: | (1) Institut für Technische Chemie und Petrolchemie der Rheinisch-Westfälischen Technischen Hochschule Aachen, Alte Maastrichter Straße 2, D-5100 Aachen, Bundesrepublik Deutschland |
| Abstract: | On acylating 2H-imidazole-4(3H)-thiones the orange to violet crystalline N-1-acyl-2H-imidazole-4(3H)-thiones1 a–18 a are formed, the thermal stability of which depends on the acyl group and the substituents in the heterocyclic ring system. Thus the N-aroyl-2,2,5-trimethyl-2H-imidazole-4(3H)-thiones13 a–16 a are stable on being heated to the melting point, while1 a–12 a are converted quantitatively to the corresponding S-aroyl-2H-imidazole-4-thiols1–12. Rearrangement is faster when the heterocyclic ring bears bulky substituents. The aliphatic N-acyl compounds17 a and18 a are thermally unstable. This N  S acyl group migration, described here for the first time, is shown to proceed by an intermolecular mechanism.Herrn Prof. Dr. Dr. h. c. mult.Hermann F. Mark zum 80. Geburtstag in Verehrung gewidmet. 88. Mitt.:F. Asinger, A. Saus, H.-J. Gräber, E. Fichtner undW. Leuchtenberger, Mh. Chem.106, 1449 (1975). Teil der DissertationE. Fichtner, Techn. Hochschule Aachen, 1974. |
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