Synthesis and transformations of bis(polychloroethylideneaminosulfonyl)- and bis(polychloroethylideneaminosulfonyl)-substituted derivatives of biphenyl, diphenyl oxide, and diphenylmethane
作者:I. B. Rosentsveig、I. V. Ushakova、A. N. Mirskova、G. G. Levkovskaya
DOI:10.1134/s1070428008020061
日期:2008.2
Reactions of N,N,N′,N′-tetrachlorobiphenyl-4,4′-disulfonamide, 4,4′-methylenebis(N,N-dichlorobenzenesulfonamide), and 4,4′-oxybis(N,N-dichlorobenzenesulfonamide) with 1,2-dichloroethylene and trichloroethylene open convenient synthetic approach to highly electrophilic bissulfony limines of dichloroacetic aldehyde and chloral: N,N′-bis(polychloroethylidene)biphenyl-4,4′-disulfonamides, 4,4′-methylenebis[N-(polychloroethylidene)benzenesulfonamides] and 4,4′-oxybis[N-(polychloroethylidene)benzenesulfonamides]. The synthetic opportunities of the bisazomethines obtained were demonstrated by examples of their reactions with water, methanol, chloroacetamide, and toluene where products of O-, N-nucleophiles addition to the azomethine bond and products of C-amidoalkylation of aromatic compound with imines were formed.
N,N,N′,N′-四氯联苯-4,4′-二磺酰胺、4,4′-亚甲基双(N,N-二氯苯磺酰胺)和4,4′-氧双(N,N-二氯苯磺酰胺)与1,2-二氯乙烯和三氯乙烯反应,开启了一种便捷的合成高亲电性二硫酰胺的合成途径,这些二硫酰胺是二氯醋醛和氯醛的衍生物:N,N′-双(多氯乙烯基)联苯-4,4′-二磺酰胺、4,4′-亚甲基双[N-(多氯乙烯基)苯磺酰胺]和4,4′-氧双[N-(多氯乙烯基)苯磺酰胺]。所获得的双亚甲基的合成机会通过其与水、甲醇、氯乙酰胺和甲苯的反应例子得到了证明,在这些反应中,形成了O-、N-亲核试剂与亚甲基键的加成产物以及芳香化合物与亚胺的C-酰基烷基化产物。