31P-labeled pyrroline N-oxides:: Synthesis of 5-diethylphosphono-5-methyl-1-pyrroline N-oxide (DEPMPO) by oxidation of diethyl (2-methylpyrrolidin-2-yl)phosphonate

被引：0
|
作者：
Barbati, S
Clément, JL
Fréjaville, C
Bouteiller, JC
Tordo, P
Michel, JC
Yadan, JC
机构：
[1] Univ Aix Marseille 1, Ctr St Jerome, Lab SREP, CNRS,UMR Chim Biol & Radicaux Libres 6517, F-13397 Marseille 20, France
[2] Oxis Int SA, Res Ctr, F-94385 Bonneuil Sur Marne, France
来源：
SYNTHESIS-STUTTGART | 1999年 / 12期
关键词：
aminophosphorylation; secondary amines; oxidations; nitrones; heterocycles; spin label; phosphorus; additions;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of DEPMPO from diethyl (2-methylpyrrolidin-2-yl)phosphonate (3), prepared by the addition of diethyl phosphite to 2-methylpyrroline, was carried out using different oxidation reagents: H2O2, m-CPBA, Oxone, 2-phenylsulfonyl-3-phenyloxaziridine (PSPO), dimethyldioxirane (DMD) and N-methylmorpholine N-oxide with catalytic amounts of tetrapropylammonium perruthenate (NMO/TPAP). The highest yield of DEPMPO (>80%) was obtained using two equivalents of PSPO or DMD. Different compounds involved in the oxidation of 3 have been isolated and characterized.
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页码：2036 / 2040
页数：5
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