144366-37-0Relevant academic research and scientific papers
Electrosynthesis and in situ chemical rearrangement of o-nitrosobenzamides
Guilbaud-Criqui, A.,Moinet, C.
, p. 101 - 110 (2007/10/02)
Primary and secondary o-nitrosobenzamides can be prepared in a "redox" cell but are unstable in the solvent used for electrolysis (acetate buffer-alcohol).At room temperature N-aryl-2-nitrosobenzamides give 2-carboxyazobenzenes.N-alkyl-2-nitrosobenzamides decompose thermally into 2-methoxy or 2-ethoxycarbonylphenylhydrazones according to the alcohol used.Similarly, methyl benzoate (or ethyl benzoate) is obtained from 2-nitrosobenzamide.A possible mechanism involves an unstable heterocycle formed by the coupling of the two nitrogen atoms (nitroso and amide) followed by cleavage of the carbonyl-nitrogen bond resulting from nucleophilic attack of the solvent (water or alcohol). Key Words: flow cell electrosynthesis / 2-nitrosobenzamides / 2-carboxyazobenzenes / 2-alkoxycarbonylphenylhydrazones / indazol-3-one
Flow cell electrosynthesis of o-substituted nitrosobenzenes. In situ reaction with sulfinic acids. Attempt to prepare heterocycles.
Guilbaud-Criqui, A.,Moinet, C.
, p. 295 - 300 (2007/10/02)
Nitrosobenzenes with CO2H 1b, CO2CH3 2b, CONR2 3b-6b, CH2CO2H 7b, CHOHCO2H 8b and NHCO2CH3 9b ortho-substituted were prepared, in a "redox" cell, from the corresponding nitro compounds.Addition of sulfinic acids to the solution after electrolyses leads to
