Article
Thermally Persistent Carbonyl Nitrene: FC(O)N
The Journal of Organic Chemistry
Document Type
Article
Disciplines
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.
Rights
One-time permission is granted only for the use specified in your request. No additional uses are granted (such as derivative works or other editions).
Copyright Owner
American Chemical Society
Copyright Date
2015
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/
Reprinted (adapted) with permission from The Journal of Organic Chemistry; 2015: 80(3); 2006-2009. Copyright 2015 American Chemical Society.