Tetrahedron p. 1365 - 1371 (1974)
Update date:2022-08-04
Topics:
McKillop
Kobylecki
Oxidation of primary nitroalkanes by acetic anhydride/sodium acetate has been found to be more complex than previously suspected. Phenylnitromethane, with acetic anhydride/sodium acetate at 60-80°, for example, gives a mixture of benzoic anhydride, triacethylhydroxylamine and acetanilide, through the mixed anhydride {A figure is presented} as a key intermediate. Evidence in support of this latter species has been obtained by carrying out the oxidation in the presence of dimethyl acetylenedicarboxylate as a 1,3-dipolarophile, when 3-phenyl-4,5-dicarbomethoxyisoxazole is formed in 82% yield. A number of other 3-alkyl- and 3-aryl-4,5-dicarbomethoxyisoxazoles have been prepared in a similar manner.
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Doi:10.1023/A:1023301531703
(2002)Doi:10.1021/jo00896a024
(1975)Doi:10.1021/jo01296a026
(1980)Doi:10.1021/jo50008a016
(1952)Doi:10.1021/ja01213a046
(1946)Doi:10.1016/j.bmc.2011.10.026
(2012)