Regiochemistry of mercury(II) oxide oxidation of unsymmetrical N,N-disubstituted hydroxylamines

被引：31

作者：

Ali, SA

Hashmi, SMA

Siddiqui, MN

Wazeer, MIM

机构：

[1] Chemistry Department, King Fahd Univ. of Petrol. and M.

来源：

TETRAHEDRON | 1996年 / 52卷 / 47期

关键词：

D O I：

10.1016/0040-4020(96)00904-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mercury(II) oxide oxidation of N,N-disubstituted hydroxylamines with the alpha and alpha' carbon atoms containing one and two hydrogen atoms, respectively, gave aldonitrones in a highly regioselective manner. Removal of the a proton is involved in the rate determining step as shown by primary kinetic isotope effect. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：14917 / 14928

页数：12

相关论文

共 24 条

[1]

ALI SA, 1994, J CHEM RES-S, P54

[2] CYCLOADDITION OF 5-SUBSTITUTED 1-PYRROLINE 1-OXIDE AND CONVERSION OF THE NITRONE CYCLOADDUCTS INTO CIS-2,5-DISUBSTITUTED AND TRANS-2,5-DISUBSTITUTED PYRROLIDINES [J].

ALI, SA ;

WAZEER, MIM .

TETRAHEDRON, 1993, 49 (20) :4339-4354

[3]

ALI SA, 1993, TETRAHEDRON LETT, V34, P5325

[4] PERACID INDUCED RING-OPENING OF ISOXAZOLIDINES - A MECHANISTIC STUDY [J].

ALI, SA ;

WAZEER, MIM .

TETRAHEDRON LETTERS, 1992, 33 (22) :3219-3222

[5] CYCLOADDITION REACTIONS OF OXIMES - POWERFUL NEW CARBON CARBON BOND FORMING METHODOLOGY [J].

ARMSTRONG, P ;

GRIGG, R ;

WARNOCK, WJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (17) :1325-1327

[6] TANDEM INTRAMOLECULAR MICHAEL ADDITION AND 1,3-DIPOLAR CYCLOADDITION REACTIONS OF OXIMES - VERSATILE NEW CARBON CARBON BOND FORMING METHODOLOGY [J].

ARMSTRONG, P ;

GRIGG, R ;

SURENDRAKUMAR, S ;

WARNOCK, WJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (17) :1327-1328

[7] ONE-FLASK TRANSFORMATION OF SECONDARY-AMINES TO NITRONES BY OXIDATION WITH HYDROGEN-PEROXIDE MEDIATED BY TRISCETYLPYRIDINIUM TETRAKIS OXODIPEROXOTUNGSTO-PHOSPHATE (PCWP) - SOME MECHANISTIC CONSIDERATIONS [J].

BALLISTRERI, FP ;

CHIACCHIO, U ;

RESCIFINA, A ;

TOMASELLI, GA ;

TOSCANO, RM .

TETRAHEDRON, 1992, 48 (40) :8677-8684

[8]

CONFALONE PN, 1988, ORG REACTIONS, V36, P1

[9]

Evans C.A., 1979, ALDRICHIM ACTA, V12, P23

[10] The nature of the alternating effect in carbon chains. Part XXII. An attempt further to define the probable mechanism of orientation in aromatic substitution. [J].

Ingold, C ;

Shaw, FR .

JOURNAL OF THE CHEMICAL SOCIETY, 1927, :2918-2926