Issue 2, 2017

Direct observation and characterisation of 3-azido-2H-azirines: postulated, but highly elusive intermediates

Abstract

For the first time, successful synthesis of an unknown class of compounds, 3-azido-2H-azirines, which are implicated as highly reactive intermediates in the thermolysis of the corresponding 1,1-diazidoethenes, has been performed. These elusive heterocycles have been detected and characterised by low-temperature NMR and in situ IR spectroscopy. Even the parent compound, 3-azido-2H-azirine, has been observed via low-temperature photolysis of 1,1-diazidoethene, as a highly reactive species with a half-life period of only 12 min at −40 °C.

Graphical abstract: Direct observation and characterisation of 3-azido-2H-azirines: postulated, but highly elusive intermediates

Supplementary files

Article information

Article type
Research Article
Submitted
12 Okt 2016
Accepted
02 Nov 2016
First published
03 Nov 2016
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2017,4, 191-195

Direct observation and characterisation of 3-azido-2H-azirines: postulated, but highly elusive intermediates

K. Weigand, N. Singh, M. Hagedorn and K. Banert, Org. Chem. Front., 2017, 4, 191 DOI: 10.1039/C6QO00625F

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