Stereoselectivity of the Diels-Alder reaction in ionic liquids with cyano moieties: effect of the charge delocalization of anions on the relation of solvent-solvent and solute-solvent interactions

被引：6

作者：

Nobuoka, Kaoru ^{[1
]}

Kitaoka, Satoshi ^{[2
]}

Yanagisako, Atsuki ^{[1
]}

Maki, Yusuke ^{[1
]}

Harran, Thomas ^{[1
]}

Ishikawa, Yuichi ^{[1
]}

机构：

[1] Oita Univ, Fac Engn, Dept Appl Chem, Oita 87011, Japan

[2] Kinki Univ, Fac Engn, Dept Biotechnol & Chem, Higashihiroshima, Japan

来源：

RSC ADVANCES | 2013年 / 3卷 / 42期

基金：

日本学术振兴会;

关键词：

DICYANAMIDE ANION; CATION-ANION; PYRROLIDINIUM SALTS; IMIDAZOLIUM; MIXTURES; WATER; CONDUCTIVITY; SPECTROSCOPY; SELECTIVITY; ALCOHOLS;

D O I：

10.1039/c3ra43523g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In imidazolium ILs, the negative charge delocalization induced by multiple electron-withdrawing cyano groups can be useful in regulating the microscopic environment in imidazolium ILs. For this anion design, the ion-counterion (solvent-solvent) interaction is weakened, the ion-solute (solvent-solute) interaction is facilitated, and the bulkiness of the anion is increased. The electrostatic interaction with the cation has a strong effect on the ion states of the ILs and the stereoselectivity in the Diels-Alder reaction. These regulation methods potentially have wide applications to various useful reactions using ILs.

引用

页码：19632 / 19638

页数：7

共 42 条

[1] The role of hydrogen bonding in controlling the selectivity of Diels-Alder reactions in room-temperature ionic liquids [J].