Reactions of Amino Alcohols in Superacid:  The Direct Observation of Dicationic Intermediates and Their Application in Synthesis

Reactions of Amino Alcohols in Superacid:  The Direct Observation of Dicationic Intermediates and Their Application in Synthesis

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....

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Veröffentlicht in:Organic letters 2001-08, Vol.3 (17), p.2781-2784
Hauptverfasser: Klumpp, Douglas A, Aguirre, Sharon L, Sanchez, Gregorio V, de Leon, Sarah J
Format: Artikel
Sprache:eng
Schlagworte:
Acids - chemistry
Amino Alcohols - chemistry
Cations, Divalent
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016408y