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Molecules 2001, 6(5), 481-495; doi:10.3390/60500481

Thermal Rearrangement of Allyl Substituted Unsymmetric 4H-1,2,4-Triazoles to the Corresponding 1H-1,2,4-triazoles

,  and *
Department of Chemistry, Norwegian University of Science and Technology, N-7491 Trondheim, Norway
* Author to whom correspondence should be addressed.
Received: 14 March 2001 / Revised: 26 April 2001 / Accepted: 26 April 2001 / Published: 30 April 2001
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A series of neat 4-(2-alkenyl) substituted 5-methyl-3-phenyl-4H-1,2,4-triazoles were thermolyzed at 320 oC producing a rearrangement products, of which the regioisomeric 1- and 2-substituted triazoles were the main products. The group migrations were rationalized in terms of consecutive SN2-type reactions. This mechanism was supported by a study of the alkylations of the triazoles which gave similar product mixtures. 4-(2-alkenyl) substituted 3-phenyl-4H-1,2,4-triazoles, on the other hand, gave predominantly elimination products.
Keywords: Thermolysis; 1; 2; 4-triazole; rearrangement Thermolysis; 1; 2; 4-triazole; rearrangement
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Jørgensen, K.B.; Olsen, R.B.; Carlsen, P.H. Thermal Rearrangement of Allyl Substituted Unsymmetric 4H-1,2,4-Triazoles to the Corresponding 1H-1,2,4-triazoles. Molecules 2001, 6, 481-495.

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