RATES AND MECHANISM OF (2+2) CYCLO-ADDITION REACTIONS OF TETRACYANOETHYLENE TO THIOENOL ETHERS

被引：22

作者：

GRAF, H ^{[1
]}

HUISGEN, R ^{[1
]}

机构：

[1] UNIV MUNICH,INST ORGAN CHEM,D-8000 MUNICH 2,FED REP GER

来源：

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

关键词：

D O I：

10.1021/jo01328a064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The high influence of solvent polarity on rate indicates the mechanistic analogy between tetracyano-ethylene cycloadditions to thioenol ethers and those to enol ethers for which a pathway with zwitterionic intermediate was established previously, whereas the structure-rate relation reveals a higher sensitivity of thioenol ethers to steric effects. © 1979, American Chemical Society. All rights reserved.

引用

页码：2594 / 2595

页数：2

共 7 条

[1] CONCENTRATION-DEPENDENCE OF RATE CONSTANTS FOR 2+2 CYCLOADDITIONS OF TETRACYANOETHYLENE
HUISGEN, R
SCHUG, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (02) : 59 - 60
[2] HUISGEN R, 1973, TETRAHEDRON LETT, P3763
[3] TETRACYANOETHYLENE AND ENOL ETHERS - MODEL FOR 2+2 CYCLOADDITIONS VIA ZWITTERIONIC INTERMEDIATES
HUISGEN, R
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1977, 10 (04) : 117 - 124
[4] STEREOCHEMISTRY OF TETRACYANOETHYLENE CYCLOADDITIONS TO THIOENOL ETHERS
HUISGEN, R
GRAF, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) : 2595 - 2596
[5] RATES OF CYCLOADDITION OF TETRACYANOETHYLENE TO ALPHA,BETA-UNSATURATED SULFIDES AND ETHERS
OKUYAMA, T
NAKADA, M
TOYOSHIMA, K
FUENO, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (23) : 4546 - 4549
[6] REICHARDT C, 1969, LOSUNGSMITTEL EFFEKT, P141
[7] TETRACYANOETHYLENE AND ENOL ETHERS - DEPENDENCE OF CYCLOADDITION RATE ON SOLVENT POLARITY
STEINER, G
HUISGEN, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) : 5056 - 5058

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