PMID: 11312954Apr 21, 2001Paper

The 1,2,4-triazolyl cation: thermolytic and photolytic studies

The Journal of Organic Chemistry
R A AbramovitchA Solé

Abstract

The generation of the 1,2,4-triazolyl cation (1) has been attempted by the thermolysis and photolysis of 1-(1,2,4-triazol-4-yl)-2,4,6-trimethylpyridinium tetrafluoroborate (2) and the thermolysis of 1- and 4-diazonium-1,2,4-triazoles, using mainly mesitylene as the trapping agent. Thermolysis of 2 gave mostly 1,2,4-triazole, together with 3-(1,2,4-triazol-4-yl)-2,4,6-trimethylpyridine, 4-(1,2,4-triazol-4-ylmethyl)-2,6-dimethylpyridine, and 4-(2,4,6-trimethylbenzyl)-2,6-dimethylpyridine. Thermolysis of each of the diazonium salts in the presence of mesitylene again gave mainly triazole together with very low yields of 1-(1,2,4-triazol-1-yl)-2,4,6-trimethylbenzene and the corresponding -4-yl isomer in about the same ratio. On the other hand, photolysis of 2 in mesitylene gave mainly 1-(1,2,4-triazol-1-yl)-2,4,6-trimethylbenzene. A photoinduced electron transfer from mesitylene to 2 has been observed and preliminary laser flash photolyses of 2 and the corresponding 2,4,6-triphenylpyridinium salt have been carried out. The observed transients are explained as arising from the first excited states of the pyridinium salts rather than from 1. Ab initio MO calculations are reported and indicate that the predicted electronic ground-stat...Continue Reading

References

May 18, 2000·The Journal of Organic Chemistry·R A AbramovitchD Bogdal
May 2, 1997·The Journal of Organic Chemistry·Ricardo J. MoranDaniel E. Falvey

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Citations

Oct 15, 2013·Environmental Toxicology and Chemistry·Laura GolsteijnMark A J Huijbregts
Mar 1, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Le Zhang, Ying-Feng Han
Jun 24, 2004·Environmental Science & Technology·José P Da Silva, Luis F Vieira Ferreira
Aug 31, 2021·The Journal of Organic Chemistry·Laura BuglioniTimothy Noël

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