Origin of the Stabilization of Vinyldiazonium Ions by β-Substitution; First Crystal Structure of an Aliphatic Diazonium Ion: β,β-Diethoxyethene-diazonium Hexachloroantimonate
The considerable contributions of the O-stabilized mesomeric resonance structures III and IV probably account for the extraordinary stability of the cation of the title compound and related systems. This is apparent from comparisons of the bond lengths and angles of the first experimentally determined structure with the results of ab initio studies. The title compound is prepared by alkylation of diazoacetate with triethyloxonium hexachloroantimonate.
R. Glaser et al., "Origin of the Stabilization of Vinyldiazonium Ions by β-Substitution; First Crystal Structure of an Aliphatic Diazonium Ion: β,β-Diethoxyethene-diazonium Hexachloroantimonate," Angewandte Chemie (International Edition in English), vol. 31, no. 6, pp. 740-743, Wiley-VCH Verlag, Jun 1992.
The definitive version is available at https://doi.org/10.1002/anie.199207401
Petroleum Research Fund of the American Chemical Society
Research Council of the University of Missouri
International Standard Serial Number (ISSN)
Article - Journal
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