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 °C 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 S(N)2-type r...

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Autores principales: Jørgensen, Kåre B., Olsen, Ragnhild B., Carlsen, Per H.J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2001
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6236431/
http://dx.doi.org/10.3390/60500481
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author Jørgensen, Kåre B.
Olsen, Ragnhild B.
Carlsen, Per H.J.
author_facet Jørgensen, Kåre B.
Olsen, Ragnhild B.
Carlsen, Per H.J.
author_sort Jørgensen, Kåre B.
collection PubMed
description A series of neat 4-(2-alkenyl) substituted 5-methyl-3-phenyl-4H-1,2,4-triazoles were thermolyzed at 320 °C 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 S(N)2-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.
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spelling pubmed-62364312018-11-20 Thermal Rearrangement of Allyl Substituted Unsymmetric 4H-1,2,4-Triazoles to the Corresponding 1H-1,2,4-triazoles. Jørgensen, Kåre B. Olsen, Ragnhild B. Carlsen, Per H.J. Molecules Article A series of neat 4-(2-alkenyl) substituted 5-methyl-3-phenyl-4H-1,2,4-triazoles were thermolyzed at 320 °C 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 S(N)2-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. MDPI 2001-04-30 /pmc/articles/PMC6236431/ http://dx.doi.org/10.3390/60500481 Text en © 2001 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes
spellingShingle Article
Jørgensen, Kåre B.
Olsen, Ragnhild B.
Carlsen, Per H.J.
Thermal Rearrangement of Allyl Substituted Unsymmetric 4H-1,2,4-Triazoles to the Corresponding 1H-1,2,4-triazoles.
title Thermal Rearrangement of Allyl Substituted Unsymmetric 4H-1,2,4-Triazoles to the Corresponding 1H-1,2,4-triazoles.
title_full Thermal Rearrangement of Allyl Substituted Unsymmetric 4H-1,2,4-Triazoles to the Corresponding 1H-1,2,4-triazoles.
title_fullStr Thermal Rearrangement of Allyl Substituted Unsymmetric 4H-1,2,4-Triazoles to the Corresponding 1H-1,2,4-triazoles.
title_full_unstemmed Thermal Rearrangement of Allyl Substituted Unsymmetric 4H-1,2,4-Triazoles to the Corresponding 1H-1,2,4-triazoles.
title_short Thermal Rearrangement of Allyl Substituted Unsymmetric 4H-1,2,4-Triazoles to the Corresponding 1H-1,2,4-triazoles.
title_sort thermal rearrangement of allyl substituted unsymmetric 4h-1,2,4-triazoles to the corresponding 1h-1,2,4-triazoles.
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6236431/
http://dx.doi.org/10.3390/60500481
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