A FACILE PREPARATION OF N-(ISOPROPOXYALKYL) AMIDES BY GENERATION AND TRAPPING OF N-ACYLIMINIUM IONS FROM IONIZATION-REARRANGEMENT REACTIONS OF N-TRIFLYLOXY AMIDES

被引：30

作者：

HOFFMAN, RV

NAYYAR, NK

机构：

[1] Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 13期

关键词：

D O I：

10.1021/jo00092a007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of hydroxamic acids were converted to N-triflyloxy amides which were heated in 2-propanol to give N-(1-isopropoxyalkyl) amides in high yields. The method is simple, direct, and extremely tolerant of structural diversity both in the N-acyl group, as well as in the 1-isopropoxyalkyl group. N-Alkylation of secondary N-(1-isopropoxyalkyl) amides can be used for converting them to tertiary N-(1-isopropoxyalkyl) amides. N-Acyliminium ions of wide structural diversity can be generated easily from N-(1-isopropoxyalkyl) amides available by this methodology.

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页码：3530 / 3539

页数：10

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