SYNTHESIS OF (E)-VINYLIC TELLURIDES AND THEIR TRANSFORMATION INTO ALPHA,BETA-UNSATURATED ESTERS AND CARBOXYLIC-ACIDS

被引：33

作者：

DABDOUB, MJ ^{[1
]}

BEGNINI, ML ^{[1
]}

CASSOL, TM ^{[1
]}

GUERRERO, PG ^{[1
]}

SILVEIRA, CC ^{[1
]}

机构：

[1] UNIV FED SANTA MARIA,DEPT QUIM,SANTA MARIA,RS,BRAZIL

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 42期

关键词：

D O I：

10.1016/0040-4039(95)01585-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Zirconium alkenyls and dienyls of E configuration, obtained by the hydrozirconation of alkynes or conjugated enynes containing a terminal triple bond undergo the Zr/Te exchange reaction by treatment with C4H9TeBr or C(4)H(9)Tel in THF at -78 degrees C. Tie Zr/Te exchange reaction proceeds with total retention of configuration and with complete stereoselectivity at the carbon 1, furnishing (E)-butyltelluro alkenes (64 - 86% yields) and (E)-1-butylteluro-1,3-dienes (68 - 75% yields). Vinylic tellurides were transformed into alpha,beta- unsaturated esters and carboxylic acids with total retention of the regio- and stereochemistry via vinyl lithium intermediates.

引用

页码：7623 / 7626

页数：4

共 20 条

[1] HYDROTELLURATION OF ACETYLENES - SYNTHESIS OF VINYLIC TELLURIDES, DIVINYL TELLURIDES, AND 1-(ORGANYLTELLURO)-1,3-BUTADIENES [J].