Synthesis of aryl-substituted piperidines by superacid activation of piperidones

被引：68

作者：

Klumpp, DA ^{[1
]}

Garza, M ^{[1
]}

Jones, A ^{[1
]}

Mendoza, S ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 18期

关键词：

D O I：

10.1021/jo990454i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diarylpiperidines (8-12) may be prepared in good to excellent yields (80-99%) by the reaction of piperidones (3d-h) with benzene and the Bronsted superacid, trifluoromethanesulfonic acid (CF3SO3H, TfOH). Tropinone (6) and quinuclidone (7) also react in good yields with benzene in TfOH to give the condensation products (13 and 14). Ketal and acetal derivatives also give condensation products (8 and 24) upon reaction with C6H6 in TfOH. The conversion of 3g to 11 is sensitive to bath acid quantity and acid strength; a mechanism is proposed for the conversion that invokes dicationic intermediates.

引用

页码：6702 / 6705

页数：4

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