REMARKABLE DIFFERENCE OF CHEMOSELECTIVITY IN THE REDUCTION OF ALPHA-BROMO KETONES WITH DIBUTYLTIN DIHYDRIDE SYSTEM

被引:13
作者
SHIBATA, I
NAKAMURA, K
BABA, A
MATSUDA, H
机构
[1] Department of Applied Chemistry, Faculty of Engineering, Osaka University. 2-1Yamadaoka, Suita, Osaka
关键词
D O I
10.1016/S0040-4039(00)97070-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Remarkably different chemoselectivities were noted in the reduction of α-bromo ketones by n-Bu2SnH2 system. Without additive, the reduction of α-bromo group took place. While. the addition of small amounts of p-Dinitrobenzene (DNB) caused the chemoselective reduction of carbonyl group. © 1990.
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页码:6381 / 6384
页数:4
相关论文
共 12 条
[1]   REACTION OF TRIBUTYLTIN OMEGA-HALOALKOXIDES WITH ISOCYANATES OR CARBODIIMIDES - A POSSIBILITY OF THE ADDITION OF AN SN-O BOND ACROSS THE C=O GROUP OF ISOCYANATE [J].
BABA, A ;
KISHIKI, H ;
SHIBATA, I ;
MATSUDA, H .
ORGANOMETALLICS, 1985, 4 (08) :1329-1333
[2]  
CASTAING MD, 1985, J ORGANOMET CHEM, V287, P49
[3]  
CASTAING MD, 1986, J ORG CHEM, V51, P1672
[4]  
Conforth J. W., 1959, J CHEM SOC, P112
[5]  
Kuivila H. G., 1970, SYNTHESIS-STUTTGART, P499
[6]   REDUCTION OF SOME ALDEHYDES AND KETONES WITH ORGANOTIN HYDRIDES [J].
KUIVILA, HG ;
BEUMEL, OF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (05) :1246-&
[7]  
NEUMANN WP, 1965, LIEBIGS ANN CHEM, V683, P11
[8]  
NEUMANN WP, 1987, SYNTHESIS-STUTTGART, P665
[9]  
PEREYRE M, 1970, TETRAHEDRON LETT, P3653
[10]  
PEREYRE M, 1987, TIN ORGANIC SYNTHESI, P33