Thermally Persistent Carbonyl Nitrene: FC(O)NThe Journal of Organic Chemistry
Publication VersionPublished Version
AbstractTransient 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.
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Copyright OwnerAmerican Chemical Society
Citation InformationHailong 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/