Journal or Book Title
The Journal of Organic Chemistry
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.
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American Chemical Society
Sun, Hailong; Zhu, Bifeng; Wu, Zhuang; Zeng, Xiaoquing; Beckers, Helmut; and Jenks, William S., "Thermally Persistent Carbonyl Nitrene: FC(O)N" (2015). Chemistry Publications. 117.