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

Cyanuric triazide reacts with several transition metal precursors, extruding one equivalent of N(2) and reducing the putative diazidotriazeneylnitrene species by two electrons, which rearranges to N-(1′H-[1,5′-bitetrazol]-5-yl)methanediiminate (biTzI(2−)) dianionic ligand, which ligates the metal an...

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Autores principales: Vaddypally, Shivaiah, Kiselev, Vitaly G., Byrne, Alex N., Goldsmith, C. Franklin, Zdilla, Michael J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179262/
https://www.ncbi.nlm.nih.gov/pubmed/34163993
http://dx.doi.org/10.1039/d0sc04949b
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author Vaddypally, Shivaiah
Kiselev, Vitaly G.
Byrne, Alex N.
Goldsmith, C. Franklin
Zdilla, Michael J.
author_facet Vaddypally, Shivaiah
Kiselev, Vitaly G.
Byrne, Alex N.
Goldsmith, C. Franklin
Zdilla, Michael J.
author_sort Vaddypally, Shivaiah
collection PubMed
description Cyanuric triazide reacts with several transition metal precursors, extruding one equivalent of N(2) and reducing the putative diazidotriazeneylnitrene species by two electrons, which rearranges to N-(1′H-[1,5′-bitetrazol]-5-yl)methanediiminate (biTzI(2−)) dianionic ligand, which ligates the metal and dimerizes, and is isolated from pyridine as [M(biTzI)](2)Py(6) (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.
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spelling pubmed-81792622021-06-22 Transition-metal-mediated reduction and reversible double-cyclization of cyanuric triazide to an asymmetric bitetrazolate involving cleavage of the six-membered aromatic ring Vaddypally, Shivaiah Kiselev, Vitaly G. Byrne, Alex N. Goldsmith, C. Franklin Zdilla, Michael J. Chem Sci Chemistry Cyanuric triazide reacts with several transition metal precursors, extruding one equivalent of N(2) and reducing the putative diazidotriazeneylnitrene species by two electrons, which rearranges to N-(1′H-[1,5′-bitetrazol]-5-yl)methanediiminate (biTzI(2−)) dianionic ligand, which ligates the metal and dimerizes, and is isolated from pyridine as [M(biTzI)](2)Py(6) (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. The Royal Society of Chemistry 2020-12-08 /pmc/articles/PMC8179262/ /pubmed/34163993 http://dx.doi.org/10.1039/d0sc04949b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Vaddypally, Shivaiah
Kiselev, Vitaly G.
Byrne, Alex N.
Goldsmith, C. Franklin
Zdilla, Michael J.
Transition-metal-mediated reduction and reversible double-cyclization of cyanuric triazide to an asymmetric bitetrazolate involving cleavage of the six-membered aromatic ring
title Transition-metal-mediated reduction and reversible double-cyclization of cyanuric triazide to an asymmetric bitetrazolate involving cleavage of the six-membered aromatic ring
title_full Transition-metal-mediated reduction and reversible double-cyclization of cyanuric triazide to an asymmetric bitetrazolate involving cleavage of the six-membered aromatic ring
title_fullStr Transition-metal-mediated reduction and reversible double-cyclization of cyanuric triazide to an asymmetric bitetrazolate involving cleavage of the six-membered aromatic ring
title_full_unstemmed Transition-metal-mediated reduction and reversible double-cyclization of cyanuric triazide to an asymmetric bitetrazolate involving cleavage of the six-membered aromatic ring
title_short Transition-metal-mediated reduction and reversible double-cyclization of cyanuric triazide to an asymmetric bitetrazolate involving cleavage of the six-membered aromatic ring
title_sort transition-metal-mediated reduction and reversible double-cyclization of cyanuric triazide to an asymmetric bitetrazolate involving cleavage of the six-membered aromatic ring
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179262/
https://www.ncbi.nlm.nih.gov/pubmed/34163993
http://dx.doi.org/10.1039/d0sc04949b
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