Begue, Didier published the artcileNitrile Imines and Nitrile Ylides: Rearrangements of Benzonitrile N-Methylimine and Benzonitrile Dimethylmethylide to Azabutadienes, Carbodiimides, and Ketenimines. Chemical Activation in Thermolysis of Azirenes, Tetrazoles, Oxazolones, Isoxazolones, and Oxadiazolones, Application In Synthesis of 1076-59-1, the publication is Journal of Organic Chemistry (2014), 79(3), 1247-1253, database is CAplus and MEDLINE.
Flash vacuum thermolysis (FVT) of 1-methyl-5-phenyltetrazole (5b), 2-methyl-5-phenyltetrazole (1b), and 3-methyl-5-phenyl-1,3,4-oxadiazol-2-(3H)-one (3b) affords the nitrile imine (2b), which rearranges in part to N-methyl-N’-phenylcarbodiimide (7b). Another part of 2b undergoes a 1,4-H shift to the diazabutadiene (13). 13 undergoes two chem. activated decompositions, to benzonitrile and CH2NH and to styrene and N2. FVT of 2,2-dimethyl-4-phenyl-oxazol-5-(2H)-one (16) at 400 °C yields 3-methyl-1-phenyl-2-azabutadiene (18) in high yield. In contrast, FVT of 3,3-dimethyl-2-phenyl-1-azirene (21) at 600 °C or 4,4-dimethyl-3-phenyl-isoxazolone (20) at 600 °C affords only a low yield of azabutadiene (18) due to chem. activated decomposition of 18 to styrene and acetonitrile. There are two reaction paths from azirene (21): one (path a) leading to nitrile ylide (17) and the major products styrene and acetonitrile and the other (path b) leading to the vinylnitrene (22) and ketenimine (23). The nitrile ylide PhC–N+C-(CH3)2 (17) is implicated as the immediate precursor of azabutadiene (18). FVT of either 3-phenylisoxazol-5-(4H)-one (25) or 2-phenylazirene (26) at 600 °C affords N-phenylketenimine (28). The nitrile ylide PhC–N+CH2 (30) is postulated as a reversibly formed intermediate. N-Phenylketenimine (28) undergoes chem. activated free radical rearrangement to benzyl cyanide. The mechanistic interpretations are supported by calculations of the energies of key intermediates and transition states.
Journal of Organic Chemistry published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C9H7NO2, Application In Synthesis of 1076-59-1.
Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem