STEREOCHEMISTRY OF TETRACYANOETHYLENE CYCLOADDITIONS TO THIOENOL ETHERS

被引：23

作者：

HUISGEN, R

GRAF, H

机构：

[1] Institut fur Organische Chemie, Universitat Minchen, 8000, Minchen, West Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 14期

关键词：

D O I：

10.1021/jo01328a065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the cyclobutane formation from ethyl cis-propenyl sulfide and cis-1-butenyl ethyl sulfide with tetracyanoethylene, the nonstereospecific portion of the cycloadduct rises with increasing solvent polarity in accordance with a zwitterionic intermediate, whereas cis → trans isomerization of the excess of thioenol ether signals the reversibility of zwitterion formation. © 1979, American Chemical Society. All rights reserved.

引用

页码：2595 / 2596

页数：2

共 5 条

[1] RATES AND MECHANISM OF (2+2) CYCLO-ADDITION REACTIONS OF TETRACYANOETHYLENE TO THIOENOL ETHERS
GRAF, H
HUISGEN, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) : 2594 - 2595
[2] REVERSIBILITY OF ZWITTERION FORMATION IN [2 + 2] CYCLOADDITION OF TETRACYANOETHYLENE TO ENOL ETHERS
HUISGEN, R
STEINER, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) : 5055 - 5056
[3] NONSTEREOSPECIFICITY IN [2 + 2] CYCLOADDITIONS OF TETRACYANOETHYLENE TO ENOL ETHERS
HUISGEN, R
STEINER, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) : 5054 - 5055
[4] TETRACYANOETHYLENE AND ENOL ETHERS - MODEL FOR 2+2 CYCLOADDITIONS VIA ZWITTERIONIC INTERMEDIATES
HUISGEN, R
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1977, 10 (04) : 117 - 124
[5] ELECTROSTATIC CATALYSIS BY IONIC AGGREGATES .5. AMINOLYSIS REACTION OF PARA-NITROPHENYL ACETATE WITH IMIDAZOLE AND PROTON-TRANSFER FROM PARA-NITROPHENOL IN LITHIUM PERCHLORATE DIETHYL ETHER SOLUTIONS
POCKER, Y
ELLSWORTH, DL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (07) : 2284 - 2293

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