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Direct observation of methoxycarbonylnitrene

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Abstract

The simplest alkoxycarbonylnitrene, CH3OC(O)N, has been generated through laser (266 and 193 nm) photolysis of CH3OC(O)N3 and CH3OC(O)NCO and subsequently characterized by IR (15N, D-labelling) and EPR (|D/hc| = 1.66 cm−1 and |E/hc| = 0.020 cm−1) spectroscopy in cryogenic matrices. Two conformers of the nitrene, with the CH3 group being in syn or anti configuration to the C[double bond, length as m-dash]O bond, have been unambiguously identified. Further UV light irradiation (365 nm) of the nitrene results in isomerization to CH3ONCO, completing the frequently explored mechanism for the Curtius-rearrangement of CH3OC(O)N3.

Graphical abstract: Direct observation of methoxycarbonylnitrene

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Publication details

The article was received on 14 Mar 2017, accepted on 06 Apr 2017 and first published on 07 Apr 2017


Article type: Communication
DOI: 10.1039/C7CC01926B
Citation: Chem. Commun., 2017, Advance Article
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    Direct observation of methoxycarbonylnitrene

    H. Li, Z. Wu, D. Li, H. Wan, J. Xu, M. Abe and X. Zeng, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC01926B

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