Transition-metal-mediated reduction and reversible double-cyclization of cyanuric triazide to an asymmetric bitetrazolate involving cleavage of the six-membered aromatic ring

Shivaiah Vaddypally, Vitaly G. Kiselev, Alex N. Byrne, C. Franklin Goldsmith, Michael J. Zdilla

Research output: Contribution to journalArticlepeer-review

Abstract

Cyanuric triazide reacts with several transition metal precursors, extruding one equivalent of N2and reducing the putative diazidotriazeneylnitrene species by two electrons, which rearranges toN-(1′H-[1,5′-bitetrazol]-5-yl)methanediiminate (biTzI2−) dianionic ligand, which ligates the metal and dimerizes, and is isolated from pyridine as [M(biTzI)]2Py6(M = Mn, Fe, Zn, Cu, Ni). Reagent scope, product analysis, and quantum chemical calculations were combined to elucidate the mechanism of formation as a two-electron reduction preceding ligand rearrangement.

Original languageEnglish
Pages (from-to)2268-2275
Number of pages8
JournalChemical Science
Volume12
Issue number6
DOIs
Publication statusPublished - 8 Dec 2020

OECD FOS+WOS

  • 1.04 CHEMICAL SCIENCES

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