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Chemistry of dicationic electrophiles: superacid-catalyzed reactions of amino acetals
Authors:Klumpp Douglas A  Sanchez Gregorio V  Aguirre Sharon L  Zhang Yun  de Leon Sarah
Affiliation:Department of Chemistry, California State Polytechnic University, 3801 West Temple Avenue, Pomona, California 91768, USA. daklumpp@csupomona.edu
Abstract: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 as condensation products in good yields (50-99%).
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