Reactions of amino alcohols in superacid: the direct observation of dicationic intermediates and their application in synthesis.
[reaction: see text]. The chemistry of amino alcohols has been studied in superacidic media, and these compounds have been found to ionize cleanly to the dication intermediates. Several dicationic species have been directly observed by low-temperature 13C NMR, including those from epinephrine (adrenaline) and synephrine. Amino alcohols react (70-99% yields) with C6H6 in triflic acid (CF3SO3H) by electrophilic aromatic substitution.
Klumpp
D A
DA
Department of Chemistry, California State Polytechnic University, 3801 West Temple Avenue, Pomona, California 91768, USA. daklumpp@csupomona.edu
Aguirre
S L
SL
Sanchez
G V
GV
de Leon
S J
SJ
D000143:Acids / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry*; D002413:Cations, Divalent
D000143:Acids; D000605:Amino Alcohols; D002413:Cations, Divalent