BENZONITRILE OXIDE Chemische Eigenschaften,Einsatz,Produktion Methoden
synthetische
The most widely employed methods of benzonitrile oxide(1) generation involve
triethylamine-mediated dehydrohalogenation of benzhydroxamoyl chloride (or bromide), readily
accessible through chlorination of benzaldoxime, or dehydration of α-nitrotoluene with PhCNO or
PhSO2Cl or ClCO2Et and a catalytic amount of Et3N (Mukaiyama reaction). A reaction of (2) with alkali
metal fluorides also provides a facile quantitative generation of (1). Although (1) has been obtained as a
crystalline solid, it is commonly generated in situ. Et3N almost immediately reacts with (2), and should
be added very slowly to an ice-cooled solution of (2) to maintain a low stationary concentration of (1) and
thereby suppress its dimerization into 3,4-diphenylfuroxan (3). Benzonitrile oxide can also be generated
photochemically by irradiation of (2) and Hexabutyldistannane, or via electrochemical oxidation of
benzaldoxime.
Synthesis Reference(s)
The Journal of Organic Chemistry, 53, p. 2468, 1988
DOI: 10.1021/jo00246a014
BENZONITRILE OXIDE Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
