Editing Nitrene (section)

==Formation==
Because nitrenes are so reactive, they are rarely isolated. Instead, they are formed as reactive intermediates during a reaction. There are two common ways to generate nitrenes:
* From [[azide]]s by [[thermolysis]] or [[photolysis]], with expulsion of [[nitrogen]] gas. This method is analogous to the formation of [[carbene]]s from [[diazo compound]]s.
* From [[isocyanate]]s, with expulsion of [[carbon monoxide]]. This method is analogous to the formation of carbenes from [[ketene]]s.
Since formation of the nitrene typically starts from a diamagnetic precursor, the direct chemical product is a singlet nitrene, which then relaxes to its ground state triplet state. As has been shown for phenylazide as a model system, the direct photoproduct of photochemical-induced N<sub>2</sub> loss can either be the singlet or triplet nitrene.<ref>{{Cite journal |last=Gritsan |first=N. P. |last2=Platz |first2=M. S. |date=2006-09-01 |title=Kinetics, Spectroscopy, and Computational Chemistry of Arylnitrenes |url=https://pubs.acs.org/doi/10.1021/cr040055%2B |journal=Chemical Reviews |volume=106 |issue=9 |pages=3844–3867 |doi=10.1021/cr040055+ |issn=0009-2665|url-access=subscription }}</ref><ref>{{Cite journal |last=Soto |first=Juan |last2=Otero |first2=Juan C. |date=2019-10-24 |title=Conservation of El-Sayed’s Rules in the Photolysis of Phenyl Azide: Two Independent Decomposition Doorways for Alternate Direct Formation of Triplet and Singlet Phenylnitrene |url=https://pubs.acs.org/doi/10.1021/acs.jpca.9b06915 |journal=The Journal of Physical Chemistry A |volume=123 |issue=42 |pages=9053–9060 |doi=10.1021/acs.jpca.9b06915 |issn=1089-5639|url-access=subscription }}</ref><ref>{{Cite journal |last=Domenianni |first=Luis I. |last2=Bauer |first2=Markus |last3=Schmidt-Räntsch |first3=Till |last4=Lindner |first4=Jörg |last5=Schneider |first5=Sven |last6=Vöhringer |first6=Peter |date=2023 |title=Photoinduced Metallonitrene Formation by N2 Elimination from Azide Diradical Ligands |url=https://onlinelibrary.wiley.com/doi/10.1002/anie.202309618 |journal=Angewandte Chemie International Edition |language=en |volume=62 |issue=42 |pages=e202309618 |doi=10.1002/anie.202309618 |issn=1521-3773|doi-access=free }}</ref> By using a triplet sensitizer, the triplet nitrene can also be formed without initial formation of the singlet nitrene.<ref>{{Cite journal |last=Murthy |first=Rajesh S. |last2=Muthukrishnan |first2=Sivaramakrishnan |last3=Rajam |first3=Sridhar |last4=Mandel |first4=Sarah M. |last5=Ault |first5=Bruce S. |last6=Gudmundsdottir |first6=Anna D. |date=2009-01-25 |title=Triplet-sensitized photolysis of alkoxycarbonyl azides in solution and matrices |url=https://linkinghub.elsevier.com/retrieve/pii/S1010603008004346 |journal=Journal of Photochemistry and Photobiology A: Chemistry |volume=201 |issue=2 |pages=157–167 |doi=10.1016/j.jphotochem.2008.10.015 |issn=1010-6030|url-access=subscription }}</ref>