CONVENIENT HALODEAMINATION AND HYDRODEAMINATION OF PRIMARY AMINES

被引:29
作者
GUZIEC, FS
WEI, DC
机构
[1] Department of Chemistry, New Mexico State University, Las Cruces
关键词
D O I
10.1021/jo00040a010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of p-toluenesulfonamides of primary amines with 2 equiv of chloroamine at room temperature in the presence of base leads to reductive deamination. If excess chloroamine is present, the corresponding alkyl or aryl halides are obtained instead in good yields. Both reactions presumably proceed via tosylhydrazine and diazene intermediates; the course of the reaction is often governed by steric hindrance. Treatment of the isolated tosylhydrazine intermediate with base and chloroamine, bromine, or iodine also leads to the corresponding halides in very good yields.
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页码:3772 / 3776
页数:5
相关论文
共 28 条
[1]   REDUCED CYCLIC COMPOUNDS .8. THE SYNTHESIS OF (+/-)-6-METHOXYPODOCARPA-5,7,13(14)-TRIENE AND (+/-)-ABIETA-5,7,13(14)-TRIENE [J].
ANSELL, MF ;
GADSBY, B .
JOURNAL OF THE CHEMICAL SOCIETY, 1959, (SEP-O) :2994-2997
[2]  
BARTON DHR, 1979, TETRAHEDRON LETT, V24, P2291
[3]  
BAUMGARTEN RJ, 1982, CHEM FUNCTIONAL G SF, P929
[4]   DEAMINATION REACTIONS OF DIFLUOROAMINE [J].
BUMGARDNER, CL ;
FREEMAN, JP ;
MARTIN, KJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (01) :97-&
[5]   REACTION OF ALKOXYHYDROPEROXIDES WITH METAL-SALTS ALKYL HALIDE PREPARATION [J].
CARDINALE, G ;
GRIMMELIKHUYSEN, JC ;
LAAN, JAM ;
VANLIER, FP ;
VANDERSTEEN, D ;
WARD, JP .
TETRAHEDRON, 1989, 45 (18) :5971-5978
[6]   OESTROGENIC CARBOXYLIC ACIDS .2. OPEN-CHAIN ANALOGUES OF DOISYNOLIC ACID [J].
CLARK, ER ;
ROBSON, RD .
JOURNAL OF THE CHEMICAL SOCIETY, 1959, (DEC) :3714-3722
[7]  
COHEN JB, 1914, J CHEM SOC, V105, P1908
[8]  
COLEMAN GH, 1939, INORG SYNTH, V1, P59
[9]  
CRAM DS, 1963, J AM CHEM SOC, V85, P3525
[10]   SIMPLE DEAMINATIONS .5. PREPARATION AND SOME PROPERTIES OF N-ALKYL-N,N-DISULFONIMIDES [J].
DECHRISTOPHER, PJ ;
ADAMEK, JP ;
LYON, GD ;
KLEIN, SA ;
BAUMGARTEN, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (24) :3525-3532