Chemistry of Dicationic Electrophiles: Superacid-Catalyzed Reactions of Amino Acetals
作者:Douglas A. Klumpp、Gregorio V. Sanchez、Sharon L. Aguirre、Yun Zhang、Sarah de Leon
DOI:10.1021/jo0111558
日期:2002.7.1
Amino acetals are shown to form highly electrophilic systems in Bronsted superacids. It is proposed that amino acetals give dicationic electrophiles, and this proposal is supported by the direct observation of a dication by low-temperature (13)C NMR. When reacted with C(6)H(6) and superacidic CF(3)SO(3)H, amino acetals are shown to provide 1-(3,3-diphenylpropyl)amines and 1-(2,2-diphenylethyl)amines
氨基缩醛显示在布朗斯台德超强酸中形成高度亲电的体系。有人提出氨基缩醛会产生二亲电子性,而这一建议得到了低温(13)C NMR直接观察二价电子的支持。当与C(6)H(6)和超酸性CF(3)SO(3)H反应时,氨基缩醛显示可提供1-(3,3-二苯丙基)胺和1-(2,2-二苯乙基)胺作为缩合产物,收率高(50-99%)。