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Thermally persistent carbonyl nitrene: FC(O)N.

Research paper by Hailong H Sun, Bifeng B Zhu, Zhuang Z Wu, Xiaoqing X Zeng, Helmut H Beckers, William S WS Jenks

Indexed on: 15 Jan '15Published on: 15 Jan '15Published in: Journal of Organic Chemistry



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.