The use of tert-butyl vinyl ether in stepwise electrophilic addition reactions

被引：4

作者：

Koikov, LN ^{[1
]}

Han, MM ^{[1
]}

Wellman, DM ^{[1
]}

Kelly, JA ^{[1
]}

Smoliakova, IP ^{[1
]}

机构：

[1] Univ N Dakota, Dept Chem, Grand Forks, ND 58202 USA

来源：

SYNTHETIC COMMUNICATIONS | 2000年 / 30卷 / 18期

关键词：

D O I：

10.1080/00397910008086984

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

tert-Butyl vinyl ether (1) reacts with p-TolSCl to give 2-tert-butoxy-2-chloroethyl p-tolyl sulfide (2). In the presence of SnCl4, 2 reacts with silyl enol ethers, allyltrimethylsilane, and vinyl ethers to form a C-C bond. In the case of vinyl ethers, the reaction proceeds through the formation of the 5-membered sulfonium salt intermediate which in turn can react with H2O, TMSCN, allyltrimethylsilane, and Grignard reagents.

引用

页码：3451 / 3464

页数：14

共 32 条

[31] INTERMOLECULAR AND INTRAMOLECULAR HETERO-DIELS-ALDER REACTIONS .36. SYNTHESIS OF DIHYDROPYRANS BY HETERO-DIELS-ALDER REACTION OF ENAMINONES - AN EFFICIENT ROUTE TO 3-AMINO SUGAR-DERIVATIVES
TIETZE, LF
HARTFIEL, U
HUBSCH, T
VOSS, E
WICHMANN, J
[J]. CHEMISCHE BERICHTE, 1991, 124 (04) : 881 - 888
[32] EFFECT OF ALKYL-GROUPS ON THE ASYMMETRIC INDUCTION COPOLYMERIZATION OF ALKYL VINYL ETHERS WITH INDENE USING (-)-MENTHOXYALUMINUM DICHLORIDE INITIATOR
YAMAGUCHI, H
DOIUCHI, T
KAWAMOTO, K
[J]. MACROMOLECULES, 1985, 18 (11) : 2120 - 2123

← 1 2 3 4 →