Chemistry of dicationic electrophiles: superacid-catalyzed reactions of amino acetals.
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%).
Klumpp
Douglas A
DA
Department of Chemistry, California State Polytechnic University, 3801 West Temple Avenue, Pomona, California 91768, USA. daklumpp@csupomona.edu
Sanchez
Gregorio V
GV
Aguirre
Sharon L
SL
Zhang
Yun
Y
de Leon
Sarah
S
D000588:Amines / Q000032:analysis* / Q000737:chemistry*; D001381:Azepines / Q000737:chemistry / Q000494:pharmacology; D001559:Benzhydryl Compounds / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D006634:Histamine H1 Antagonists / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010276:Parasympatholytics / Q000737:chemistry / Q000494:pharmacology; D011437:Propylamines / Q000737:chemistry / Q000494:pharmacology; D013696:Temperature
D000588:Amines; D001381:Azepines; D001559:Benzhydryl Compounds; D006634:Histamine H1 Antagonists; D010276:Parasympatholytics; D011437:Propylamines; C004952:prozapine; C470220:fenpiprane; C005547:tolpropamine