Reactions of amino alcohols in superacid: The direct observation of dicationic intermediates and their application in synthesis

Authors
Klumpp, DA Aguirre, SL Von Sanchez, G de Leon, SJ
Citation
Da. Klumpp et al., Reactions of amino alcohols in superacid: The direct observation of dicationic intermediates and their application in synthesis, ORG LETT, 3(17), 2001, pp. 2781-2784
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
17
Year of publication
2001
Pages
2781 - 2784
Database
ISI
SICI code
1523-7060(20010823)3:17<2781:ROAAIS>2.0.ZU;2-3
Abstract
[GRAPHICS] The chemistry of amino alcohols has been studied in superacidic media, and these compounds have been found to ionize cleanly to the dication intermedi ates. Several dicationic species have been directly observed by low-tempera ture C-13 NMR, including those from epinephrine (adrenaline) and synephrine . Amino alcohols react (70-99% yields) with C6H6 in triflic acid (CF3SO3H) by electrophilic aromatic substitution.