The Synthesis and photochemistry of several di- and tri- substituted 1,2,4-triazoles -- a mechanistic study

Hayes, Bryan D.

Student Work

The Synthesis and photochemistry of several di- and tri- substituted 1,2,4-triazoles -- a mechanistic study

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Following one suggested procedure, 1,3,5-triphenyl-1,2,4- triazole could be formed via two different mechanistic pathways. Both mechanisms yield the same triazole because the three substituents are phenyl groups. If one of the substituents is changed to a methyl group through use of different starting materials, two products are possible, 5-methyl-1,3-diphenyl-1,2,4-triazole or 3-methyl-1,5- diphenyl-1,2,4 triazole. A procedure was devised for which there was one possible mechanism leading only to 5-methyl-1,3-diphenyl-1,2,4-triazole. Comparison of the NMR spectra and melting point data confirmed that both procedures gave 5-methyl-1,3-diphenyl-1,2,4-triazole. Neither 1,3,5-triphenyl-1,2,4-triazole nor 1,5-diphenyl-1,2,4- triazole underwent a photoisomerization reaction when exposed to UV light at 254 nm or 300 nm.

This report represents the work of one or more WPI undergraduate students submitted to the faculty as evidence of completion of a degree requirement. WPI routinely publishes these reports on its website without editorial or peer review.

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