Direct observation and characterisation of 3-azido-2H-azirines: postulated, but highly elusive intermediates12. Issue 2 (9th November 2016)

• Record Type: Journal Article
• Authors: Weigand, Kevin; Singh, Neeraj; Hagedorn, Manfred; Banert, Klaus
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 2(2017)
• Page Start: 191
• Page End: 195
• Publication Date: 2016-11-09
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c6qo00625f
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The title compounds, including the parent 3-azido-2 H -azirine, were generated by low-temperature photolysis of the corresponding 1, 1-diazidoethenes, and characterised not only by trapping reactions, but also by direct detection using NMR and in situ IR spectroscopy. Abstract : For the first time, successful synthesis of an unknown class of compounds, 3-azido-2 H -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-2 H -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.