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

被引：29

作者：

Klumpp, DA ^{[1
]}

Aguirre, SL ^{[1
]}

Von Sanchez, G ^{[1
]}

de Leon, SJ ^{[1
]}

机构：

[1] Calif State Polytech Univ Pomona, Dept Chem, Pomona, CA 91768 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 17期

关键词：

D O I：

10.1021/ol016408y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 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 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.

引用

页码：2781 / 2784

页数：4

共 18 条

[1] COMPARISON OF THE EFFECTIVENESS OF SULFURIC-ACID AND TRIFLUORO-METHANESULFONIC ACID IN KOCH CARBOXYLATION REACTIONS [J].

BOOTH, BL ;

ELFEKKY, TA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (10) :2441-2446

[2] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[3] ALPHA-CARBONYL CARBOCATIONS .4. NMR DETECTION AND REACTIVITIES OF DIARYL ALPHA-CARBONYL CATIONS [J].

DAO, LH ;

MALEKI, M ;

HOPKINSON, AC ;

LEERUFF, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (17) :5237-5242

[4]

Frisch M.J., 2016, Gaussian 16 Revision C. 01. 2016, V16, P01

[5]

Giringauz A, 1997, MED CHEM

[6] HERSTELLUNG VON DIARYL-ALKYLAMINEN AUS ARYLALKANOLAMINEN [J].

KLOSA, J .

NATURWISSENSCHAFTEN, 1966, 53 (17) :433-&

[7] EINE NEUE SYNTHESE VON DIPHENYLISOPROPYLAMINEN [J].

KLOSA, J .

JOURNAL FUR PRAKTISCHE CHEMIE, 1966, 34 (5-6) :335-&

[8] Synthesis of aryl-substituted piperidines by superacid activation of piperidones [J].

Klumpp, DA ;

Garza, M ;

Jones, A ;

Mendoza, S .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6702-6705

[9] 3-pyridinecarboxaldehyde: A model system for superelectrophilic activation and the observation of a diprotonated electrophile [J].

Klumpp, DA ;

Lau, SF .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) :7309-7311

[10]

Klumpp DA, 2000, SYNTHESIS-STUTTGART, P1117

← 1 2 →