Attempted Generation of Substituted 1,2,3-Triazolium-1-methanides: a New Ring Expansion to 2,3-Dihydro-1,2,4-triazines: ab initio Calculations on 1,2,3-Triazolium-1-oxide, -1-imide, and -1-methanide 1,3-Dipoles and a Striking Illustration of the Hammond Principle in the Cyclisation of H.

Article abstract of DOI:10.1039/c39900000882

Treatment of 1-methyl-1,2,3-triazolium salts with ethoxide gave 2,3-dihydro-1,2,4-triazines via 1,2,5-triazahexa-1,3,5-trienes but the expected 1,2,3-triazolium-1-methanide 1,3-dipoles were not detected and ab initio calculations suggest that they are thermodynamically unfavoured; the X-ray crystal structure of (6a), a dihydro-1,2,4-triazine, is reported.

Full text of DOI:10.1039/c39900000882

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