A 1ST EXAMPLE OF CATALYTIC YLIDE EPOXIDATION REACTION - FACILE SYNTHESIS OF VINYL EPOXIDES FROM ALDEHYDES CATALYZED BY DIISOBUTYL TELLURIDE

被引:32
作者
ZHOU, ZL [1 ]
SHI, LL [1 ]
HUANG, YZ [1 ]
机构
[1] ACAD SINICA,SHANGHAI INST ORGAN CHEM,ORGANOMETALL CHEM LAB,345 LINGLING LU,SHANGHAI 200032,PEOPLES R CHINA
关键词
D O I
10.1016/S0040-4039(00)97324-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of cesium carbonate, a variety of aldehydes can be epoxidized directly with allyl bromide at 50-degrees-C under solid-liquid phase transfer condition by use of a catalytic amount of diisobutyl telluride to afford vinyl epoxides in good yields with predominant cis stereoselectivity.
引用
收藏
页码:7657 / 7660
页数:4
相关论文
共 16 条
[1]   SYNTHESIS AND REACTIONS OF UNSTABILIZED ALPHA-SELENONIO ALKYLIDES [J].
DUMONT, W ;
BAYET, P ;
KRIEF, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1974, 13 (04) :274-275
[2]   SYNTHETIC APPLICATIONS OF ORGANOTELLURIUM COMPOUNDS .1. A FACILE SYNTHESIS OF ALPHA,BETA-UNSATURATED ESTERS, KETONES, AND NITRILES [J].
HUANG, X ;
XIE, LH ;
WU, H .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4862-4864
[3]   THE APPLICATION OF ELEMENTO-ORGANIC COMPOUNDS OF THE 15TH AND 16TH GROUPS IN ORGANIC-SYNTHESIS .69. AN EFFICIENT OLEFINATION METHOD CATALYZED BY DIBUTYL TELLURIDE [J].
HUANG, YZ ;
SHI, LL ;
LI, SW ;
WEN, XQ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (12) :2397-2399
[4]  
HUANG YZ, 1982, ADV ORGANOMET CHEM, V20, P115
[5]  
JOHNSON AW, 1966, YLIDE CHEM
[6]   ARSONIUM YLIDES (WITH SOME MENTION ALSO OF ARSINIMINES, STIBONIUM AND BISMUTHONIUM YLIDES) [J].
LLOYD, D ;
GOSNEY, I ;
ORMISTON, RA .
CHEMICAL SOCIETY REVIEWS, 1987, 16 (01) :45-74
[7]   SYNTHESIS OF ALPHA,BETA-UNSATURATED CARBOXAMIDES USING DIALKYLTELLURONIUM CARBAMOYLMETHYLIDE [J].
OSUKA, A ;
HANASAKI, Y ;
SUZUKI, H .
NIPPON KAGAKU KAISHI, 1987, (07) :1505-1507
[8]   DIALKYLTELLURONIUM ALLYLIDE AS A NOVEL REAGENT FOR SYNTHESIS OF ALPHA,BETA-UNSATURATED EPOXIDES [J].
OSUKA, A ;
SUZUKI, H .
TETRAHEDRON LETTERS, 1983, 24 (46) :5109-5112
[9]   A NEW SYNTHESIS OF ALPHA,BETA-UNSATURATED CARBOXYLIC ESTERS USING DIALKYLTELLURONIUM CARBETHOXYMETHYLIDE [J].
OSUKA, A ;
MORI, Y ;
SHIMIZU, H ;
SUZUKI, H .
TETRAHEDRON LETTERS, 1983, 24 (25) :2599-2602
[10]   SYNTHESIS OF VINYLIC EPOXIDES VIA ARSONIUM YLIDES [J].
OUSSET, JB ;
MIOSKOWSKI, C ;
SOLLADIE, G .
TETRAHEDRON LETTERS, 1983, 24 (41) :4419-4422