UNIQUE TEMPLATE EFFECTS OF DISTANNOXANE CATALYSTS IN TRANSESTERIFICATION OF DIOL ESTERS

被引:29
作者
OTERA, J
DANOH, N
NOZAKI, H
机构
[1] Department of Applied Chemistry, Okayama University of Science, Okayama, 700, Ridai-cho
关键词
D O I
10.1016/S0040-4020(01)89888-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,n-Diol diacetates (n = 2,3,4) are selectively converted into the corresponding monoacetates by distannoxane-catalyzed transesterification. Such unique selectivity is not encountered with 1,n-diol diacetates where n greater-than-or-equal-to 5. A great difference in reactivity is also seen in the transesterifiaction between methyl butyrate and l,n-diol monoacetates: the ethylene glycol derivative sluggishly undergoes transesterification whereas higher homologs react smoothly. The unique template effects of the catalysts are discussed in terms of cooperation of two different tin atoms which are located in the proximity.
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页码:3065 / 3074
页数:10
相关论文
共 13 条
[1]  
BABLER JH, 1979, TETRAHEDRON LETT, P1971
[2]   USE OF INSOLUBLE POLYMER SUPPORTS IN GENERAL ORGANIC-SYNTHESIS [J].
LEZNOFF, CC .
ACCOUNTS OF CHEMICAL RESEARCH, 1978, 11 (09) :327-333
[3]   SELECTIVE MONOETHERIFICATION OF 1,N-DIOLS CATALYZED BY ALUMINUM SULFATE SUPPORTED ON SILICA-GEL [J].
NISHIGUCHI, T ;
KAWAMINE, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (24) :1766-1767
[4]   SELECTIVE MONOACYLATION OF 1,NORMAL-DIOLS CATALYZED BY METALLIC SULFATES SUPPORTED ON SILICA-GEL [J].
NISHIGUCHI, T ;
TAYA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (25) :9102-9103
[5]   METHYLATION OF ALCOHOLS, PHENOLS, AND CARBOXYLIC-ACIDS, AND SELECTIVE MONOMETHYLATION OF DIOLS AND DICARBOXYLIC-ACIDS WITH DIMETHYL SULFATE BY USE OF ALUMINA [J].
OGAWA, H ;
ICHIMURA, Y ;
CHIHARA, T ;
TERATANI, S ;
TAYA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (08) :2481-2483
[6]   SELECTIVE MONOMETHYL ESTERIFICATION OF DICARBOXYLIC-ACIDS BY USE OF MONOCARBOXYLATE CHEMISORPTION ON ALUMINA [J].
OGAWA, H ;
CHIHARA, T ;
TAYA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1365-1369
[7]  
OGAWA H, 1986, J CHEM SOC CHEM COMM, V1337
[8]   NOVEL TEMPLATE EFFECTS OF DISTANNOXANE CATALYSTS IN HIGHLY EFFICIENT TRANSESTERIFICATION AND ESTERIFICATION [J].
OTERA, J ;
DANOH, N ;
NOZAKI, H .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5307-5311
[9]   DISTANNOXANE AS REVERSE MICELLE-TYPE CATALYST - NOVEL SOLVENT EFFECT ON REACTION-RATE OF TRANS-ESTERIFICATION [J].
OTERA, J ;
IOKA, S ;
NOZAKI, H .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4013-4014
[10]   NOVEL DISTANNOXANE-CATALYZED TRANSESTERIFICATION AND A NEW ENTRY TO ALPHA,BETA-UNSATURATED CARBOXYLIC-ACIDS [J].
OTERA, J ;
YANO, T ;
KAWABATA, A ;
NOZAKI, H .
TETRAHEDRON LETTERS, 1986, 27 (21) :2383-2386