Issue 35, 2017
From the journal:

Chemical Communications

Direct observation of methoxycarbonylnitrene†

Hongmin Li,a   Zhuang Wu,a   Dingqing Li,a   Huabin Wan,a   Jian Xu,a   Manabu Abeb  and  Xiaoqing Zeng ORCID logo *a  

* Corresponding authors

a College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Jiangsu 215123, China
E-mail: xqzeng@suda.edu.cn

b Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima, Hiroshima 739-8526, Japan

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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C7CC01926B
Article type
Communication
Submitted
14 Mar 2017
Accepted
06 Apr 2017
First published
07 Apr 2017

Chem. Commun., 2017,53, 4783-4786

Permissions

Request permissions

Direct observation of methoxycarbonylnitrene

H. Li, Z. Wu, D. Li, H. Wan, J. Xu, M. Abe and X. Zeng, Chem. Commun., 2017, 53, 4783 DOI: 10.1039/C7CC01926B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements