113353-97-2Relevant academic research and scientific papers
Cycloaddition of Methyl Azide to 5-Alkylidene-1,4-dihydro-1,4-dimethyl-5H-tetrazoles
Quast, Helmut,Bieber, Lothar,Meichsner, Georg,Regnat, Dieter
, p. 1285 - 1290 (2007/10/02)
Sodium hydride deprotonates the 5-alkyl-1,4-dimethyltetrazolium ions 4 affording the air-sensitive, yellow, distillable 5-alkylidene-1,4-dihydro-5H-tetrazoles 1.In addition, small amounts of the spiro compound 5a are formed through cleavage of 4a by nucleophiles yielding methyl azide followed by cycloaddition of the latter to give 1a.In separate experiments, methyl azide reacts smoothly with 1 at temperatures as low as 0-20 deg C producing the spiro compounds 5 which exhibit suprising thermal stability.The structures of the cycloadducts 5 are based on spectra and the base-induced cleavage of 5b into methyl azide and aminotriazole 16.The latter is synthesized independently from tert-butylacetonitrile and methyl azide.
