165531-65-7Relevant articles and documents
2-(N-Methylanilino)-2-phenylsulfanylacetonitrile, A Reagent Tested for Electrophilic, Nucleophilic, and Radical Reactions
Chen, Chih-Cheng,Chen, Same-Ting,Chuang, Tsung-Hsun,Fang, Jim-Min
, p. 2217 - 2222 (2007/10/02)
2-(N-Methylanilino)-2-phenylsulfanylacetonitrile 1 has been readily prepared from 2-(N-methylanilino)acetonitrile and diphenyl disulfide.Alkylation of the anion of 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated α-aminoalkenenitriles of 2E-configuration.Autoxidation of 1 in the presence of alkoxide ions afforded alkyl N-methyl-N-phenylcarbamates.Nucleophilic substitution of 1 with Grignard reagent or appropriate silyl compounds were promoted by CuI or Lewis acids to give varied α-amino nitriles.The 4-oxo-2-aminonitriles 9 obtained by condensation of 1 and titanium enolates can be considered as derivatives of 1,3-dicarbonyl compounds with the aldehyde group being activated to give an amino nitrile umpolung.When 1 was treated with tributylstannane, the corresponding amino nitrile α-radical was formed and the self-coupling product was isolated.