Next Article in Journal
Molecular Polarizability of Sc and C (Fullerene and Graphite) Clusters
Previous Article in Journal
Synthesis of 2,4,6-Tris(4-N-isopropylamidinophenyl)pyrimidine trihydrochloride
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
Download PDF [77 KB, uploaded 18 June 2014]


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
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
MDPI and ACS Style

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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here


Cited By

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert