4-Pyridylnitrene and 2-pyrazinylcarbene.
Both flash vacuum thermolysis (FVT) and matrix photolysis generate 2-diazomethylpyrazine (22) from 1,2,3-triazolo[1,5-a]pyrazine (24). FVT of 4-azidopyridine (18) as well as of 24 or 2-(5-tetrazolyl)pyrazine (23) affords the products expected from the nitrene, i.e., 4,4'-azopyridine and 2- and 3-cyanopyrroles. Matrix photolyses of both 18 and 24 result in ring expansion of 4-pyridylnitrene/2-pyrazinylcarbene to 1,5-diazacyclohepta-1,2,4,6-tetraene (20). Further photolysis causes ring opening to the ketenimine 27.
7 references, click to expand
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3-pyridylcarbene and 3-pyridylnitrene: ring opening to nitrile ylides.J Am Chem Soc. 2003 Jul 30;125(30):9083-9 PMID: 15369365
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2-Pyridylnitrene from tetrazolo[1,5-a]pyridine and pyrido[2,3-a][1,2,4]oxadiazol-2-one.J Org Chem. 2008 Aug 15;73(16):6265-7 PMID: 18646825
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Different behavior of nitrenes and carbenes on photolysis and thermolysis: formation of azirine, ylidic cumulene, and cyclic ketenimine and the rearrangement of 6-phenanthridylcarbene to 9-phenanthrylnitrene.J Org Chem. 2005 Sep 30;70(20):7947-55 PMID: 16277314
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Nitrenes, carbenes, diradicals, and ylides. Interconversions of reactive intermediates.Acc Chem Res. 2011 Jun 21;44(6):393-404 PMID: 21452850
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2-Pyridylnitrene and 3-pyridazylcarbene and their relationship via ring-expansion, ring-opening, ring-contraction, and fragmentation.J Org Chem. 2010 Mar 5;75(5):1600-11 PMID: 20131858
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2-quinoxalinylnitrenes and 4-quinazolinylnitrenes: rearrangement to cyclic and acyclic carbodiimides and ring-opening to nitrile ylides.J Am Chem Soc. 2011 Apr 13;133(14):5413-24 PMID: 21417327
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Rearrangements and interconversions of carbenes and nitrenes.Top Curr Chem. 1976;62:173-251 PMID: 941142
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