Thermally Persistent Carbonyl Nitrene: FC(O)N

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2015-01-13
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Sun, Hailong
Zhu, Bifeng
Wu, Zhuang
Zeng, Xiaoquing
Beckers, Helmut
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Jenks, William
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Chemistry

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

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Thu Jan 01 00:00:00 UTC 2015
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