124706-38-3Relevant academic research and scientific papers
The 1,2,4-triazolyl cation: Thermolytic and photolytic studies
Abramovitch,Beckert,Gibson Jr.,Belcher,Hundt,Sierra,Olivella,Pennington,Sole
, p. 1242 - 1251 (2007/10/03)
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-state of the triazolyl cation is a triplet state of B1 symmetry with five π electrons, which corresponds to a diradical cation (1c). Possible mechanisms for the formation of the various products are proposed.
Electrophilic amination. Direct primary amination of arenes using phthalimide derivatives
Abramovitch, Rudolph A.,Beckert, Joseph M.,Chinnasamy, Pennamuthiriar,Xiaohua, He,Pennington, William,Sanjivamurthy, A.R.Vinutha
, p. 623 - 628 (2007/10/02)
Electrophi1ic primary amination of arenes has been achieved by the thermolysis or photolysis of N-sulfonyloxyphthalimide in the presence of trifluoromethane-sulfonic acid or of 1-phthalimido-2,4,6-triphenylpyridinium tetrafluoroborate in the presence of CF3CO2H. The diacylnitrenium 10 was probably formed in the latter case. The structure of one of the byproducts, 7 was established by single crystal X-ray analysis.
