SOLVENT EFFECTS ON ENDO/EXO-SELECTIVITIES AND REGIO-SELECTIVITIES OF DIELS-ALDER REACTIONS OF CARBONYL-CONTAINING DIENOPHILES

被引：43

作者：

CATIVIELA, C ^{[1
]}

GARCIA, JI ^{[1
]}

MAYORAL, JA ^{[1
]}

SALVATELLA, L ^{[1
]}

机构：

[1] UNIV ZARAGOZA,CSIC,INST CIENCIA MAT ARAGON,DEPT QUIM ORGAN,E-50009 ZARAGOZA,SPAIN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1994年 / 04期

关键词：

D O I：

10.1039/p29940000847

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selectivity of Diels-Alder reactions of methyl vinyl ketone and methyl acrylate, with cyclopentadiene and isoprene, have been studied in 18 pure solvents and aqueous mixtures. The results obtained have been analysed by means of regression models, using empirical solvent parameters. The endo/exo selectivity mainly depends on the solvophobic (S-p) and hydrogen bond donor (alpha) properties of the solvent. The influence of the dipolarity (pi*) is only observed in the reactions with methyl acrylate. Regioselectivity almost exclusively depends on the hydrogen bond donor ability of the solvent. The double coordination observed with highly hydrogen bond donating solvents in the case of methyl vinyl ketone greatly increases the para/meta isomer ratio.

引用

页码：847 / 851

页数：5

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