Absence of triazirine intermediates in the photolytic formation of azides from mesoionic 3-substituted 1,2,3,4-oxatriazolylio-5-oxides : Isotope labelling experiments |
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Authors: | C. Bjerre C. Christophersen B. Hansen N. Harrit F.M. Nicolaisen A. Holm |
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Affiliation: | The University of Copenhagen, The H.C. Ørsted Institute, Chemical Laboratory II and V, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark |
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Abstract: | Irradiation of 3-phenyl-1,2,3,4-oxatriazolylio-5-oxide (1) leads to formation of CO2, N2O, phenyl azide and phenyl isocyanate. The two latter compounds are observed only in low yields because of secondary photolytic reactions. Photolysis in CCl4 or Cl2CCCl2 of 2-15N labelled (1) leads almost exclusively to the formation of 3-15H labelled phenyl azide identified by IR spectroscopy on comparison with authentic 1-15N, 2-15N and 3-15N labelled phenyl azides, respectively. These results show that phenyl azide is formed photolytically from (1) via phenyl migration and not via “antiaromatic”, phenyl triazirine (2). |
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