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Facile Conversion of Aryl Amines Having No α-Methylene to Aryl Nitriles.

ABSTRACT: Dimethyl carbonimidodithioates, 2 derived from various primary aryl amines (1) by reacting with carbon disulfide and methyl iodide in dimethyl formamide in the presence of concentrated sodium hydroxide, are converted to the diaziridine derivatives, 3 by reacting with hydrazine in ethanol. The diaziridines, 3 on oxidation with lead tetraacetate in refluxing xylene, extrudes nitrogen, and intramolecular stabilization, particularly 1,2-carbon migration, takes place to give the product, 5. The reaction may take place through the intermediates, diazirines, 4, which have not been isolated. This work provides a new approach for the conversion of aryl amines having no α-methylene to aryl nitriles.

SUBMITTER: Moirangthem SS

PROVIDER: S-EPMC9453805 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Facile Conversion of Aryl Amines Having No α-Methylene to Aryl Nitriles.

Moirangthem Shyamkanhai S SS Ahanthem Dini D Khongbantabam Sanatombi D SD Laitonjam Warjeet S WS

ACS omega 20220822 35

Dimethyl carbonimidodithioates, 2 derived from various primary aryl amines (1) by reacting with carbon disulfide and methyl iodide in dimethyl formamide in the presence of concentrated sodium hydroxide, are converted to the diaziridine derivatives, 3 by reacting with hydrazine in ethanol. The diaziridines, 3 on oxidation with lead tetraacetate in refluxing xylene, extrudes nitrogen, and intramolecular stabilization, particularly 1,2-carbon migration, takes place to gi ...[more]

PMID: 36092588

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