Cantillo, David published the artcileMechanistic Insights on Azide-Nitrile Cycloadditions: On the Dialkyltin Oxide-Trimethylsilyl Azide Route and a New Vilsmeier-Haack-Type Organocatalyst, Computed Properties of 2251-79-8, the publication is Journal of the American Chemical Society (2011), 133(12), 4465-4475, database is CAplus and MEDLINE.
The mechanism of the azide-nitrile cycloaddition mediated by the known dialkylltin oxide-trimethylsilyl azide catalyst system was addressed through DFT calculations The catalytic cycle for this tin/silicon complex-based mechanism was thoroughly examined, disclosing the most plausible intermediates and the energetics involved in the rate enhancement. A new catalyst, 5-azido-1-methyl-3,4-dihydro-2H-pyrrolium azide, is presented for the formation of tetrazoles by cycloaddition of sodium azide with organic nitriles under neutral conditions. The efficiency of this organocatalyst, generated in situ from N-methyl-2-pyrrolidone (NMP), sodium azide, and trimethylsilyl chloride under reaction conditions, was examined by preparation of 5-substituted-1H-tetrazoles. The desired target structures were obtained in high yields within 15-25 min employing controlled microwave heating. An in depth computational anal. of the proposed catalytic cycle also was addressed to understand the nature of the rate acceleration. The computed energy barriers were compared to the dialkylltin oxide-trimethylsilyl azide metal-based catalyst system. Both the tin/silicon species and the new organocatalyst accelerate the azide-nitrile coupling by activating the nitrile substrate. As compared to the dialkylltin oxide-trimethylsilyl azide method, the organocatalytic system presented herein has the advantage of higher reactivity, in situ generation from inexpensive materials, and low toxicity.
Journal of the American Chemical Society published new progress about 2251-79-8. 2251-79-8 belongs to isoxazole, auxiliary class Trifluoromethyl,Fluoride,Benzene, name is 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, and the molecular formula is C8H5F3N4, Computed Properties of 2251-79-8.
Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem