17720-63-7Relevant academic research and scientific papers
Azides. Part VIII. Thermolysis of ethyl azidoformate in acetic and propionic anhydrides: facilitation of intramolecular cyclization of the resultant carbethoxynitrene to 2-oxazolidinone
Ayyangar, N. R.,Brahme, K. C.,Srinivasan, K. V.
, p. 1463 - 1468 (2007/10/02)
The thermolysis of ethyl azidoformate in acetic and propionic anhydrides as solvent yielded the corresponding N-acyl-2-oxazolidinones (2a,b) in relatively significant yields.The other major products isolated were N-carboxyethyl-N,O-diacyl hydroxylamine (1a.b) and N,N,O-triacetyl hydroxylamine (3).The intramolecular cyclization is facilitated by the solvent.
BYPRODUCTS IN THE PREPARATION OF PENTA-O-ACETYL-D-HEXONONITRILES FROM D-GALACTOSE AND D-GLUCOSE
Furneaux, Richard H.
, p. 241 - 256 (2007/10/02)
The procedures commonly employed for preparing per-O-acetylated aldononitrile derivates of D-galactose and D-glucose for use in g.l.c. analysis involve oxime formation, and acetylation.They do not, however, give the nitriles as the sole products, as is generally assumed.Instead, N-hydroxy-D-glycosylamine hexaacetates are formed as byproducts, in part by a kinetically controlled ring-closure of the sugar oxime, concomitant with acetylation.From preparative isolation of the products, D-galactose gave the nitrile (67 percent) and the β-furanose (16 percent), α-furanose (1 percent), and β-pyranose (2 percent) isomers of the cyclic hexaacetate, whereas D-glucosegave the nitrile (63 percent), and the β-furanose (14 percent), and β-pyranose (8 percent) isomers.
An investigation of the reaction of primary nitroalkanes with acetic anhydride/sodium acetate
McKillop,Kobylecki
, p. 1365 - 1371 (2007/10/05)
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.
