A HIGHLY EFFECTIVE QUENCHING METHOD OF 1,3-DIPOLAR CYCLOADDITIONS OF NITRILE OXIDES OR NITRILE OXIDE-LEWIS-ACID COMPLEXES BY USE OF 2-PROPENYLOXYMAGNESIUM BROMIDE

被引：15

作者：

KANEMASA, S ^{[1
]}

NISHIUCHI, M ^{[1
]}

机构：

[1] KYUSHU UNIV,INTERDISCIPLINARY GRAD SCH ENGN SCI,DEPT MOLEC SCI & TECHNOL,KASUGA 816,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 25期

关键词：

NITRILE OXIDE; DIPOLAR CYCLOADDITION; LEWIS ACID COMPLEX; TERMINATION; QUENCHER; ALLYL ALCOHOL; MAGNESIUM ALKOXIDE;

D O I：

10.1016/S0040-4039(00)60603-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Propenyloxymagnesium bromide, readily prepared by treating 2-propen-1-ol with EtMgBr, is a highly effective quencher of nitrile oxide cycloadditions since this alkoxide is much more reactive to nitrile oxides than any other ever known dipolarophiles of the electron-deficient, electron-rich, and strained types, including 3-buten-2-one, ethyl vinyl ether, and norbornene, respectively. This quencher is also effectively utilized to terminate the dipolar cycloadditions of nitrile oxide/Lewis acid complexes.

引用

页码：4011 / 4014

页数：4

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