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Article
Thermally Persistent Carbonyl Nitrene: FC(O)N
The Journal of Organic Chemistry
  • Hailong Sun, Soochow University
  • Bifeng Zhu, Soochow University
  • Zhuang Wu, Soochow University
  • Xiaoquing Zeng, Soochow University
  • Helmut Beckers, Freie Kunst-Studienstatte Ottersberg
  • William S. Jenks, Iowa State University
Document Type
Article
Publication Version
Published Version
Publication Date
1-13-2015
DOI
10.1021/jo502821y
Abstract
Transient carbonyl nitrenes RC(O)N, formed during thermal- or photoinduced decomposition of carbonyl azides RC(O)N3, are highly liable to the Curtius rearrangement, producing isocyanates RNCO in almost quantitative yield. Contrary to common belief, we found a thermally persistent triplet carbonyl nitrene, FC(O)N, that can be produced by flash pyrolysis of FC(O)N3 in 49% yield. The computed CBS-QB3 activation barrier for the thermal decomposition of FC(O)N3 to FC(O)N is 29 kJ mol–1 lower than that for a concerted pathway producing FNCO.
Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry; 2015: 80(3); 2006-2009. Copyright 2015 American Chemical Society.

Rights
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Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
Hailong Sun, Bifeng Zhu, Zhuang Wu, Xiaoquing Zeng, et al.. "Thermally Persistent Carbonyl Nitrene: FC(O)N" The Journal of Organic Chemistry Vol. 80 Iss. 3 (2015) p. 2006 - 2009
Available at: http://works.bepress.com/william_jenks/21/