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

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 rea...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2001-05, Vol.6 (5), p.481-495
Main Authors: Jørgensen, Kåre B., Olsen, Ragnhild B., Carlsen, Per H.J.
Format: Article
Language:English
Subjects:
4-triazole
rearrangement
Thermolysis
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/60500481