Friedel-Crafts reactions in ionic liquids: the counter-ion effect on the dealkylation and acylation of methyl dehydroabietate

被引：20

作者：

Baleizao, C ^{[1
]}

Pires, N ^{[1
]}

Gigante, B ^{[1
]}

Curto, MJM ^{[1
]}

机构：

[1] INETI, Dept Tecnol Ind Quim, P-1649038 Lisbon, Portugal

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 22期

关键词：

ionic liquids; Friedel-Crafts; counter-ion effect; methyl dehydroabietate;

D O I：

10.1016/j.tetlet.2004.03.185

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ionic liquids with different counter-ion and alkyl substitutes were tested as solvents in the dealkylation and acylation of methyl dehydroabietate, a useful and inexpensive building block for the synthesis of higher diterpenes derivatives. Ionic liquids with halogen counter-ions are very active in both reactions with high rate constant and conversion, avoiding the use of the conventional solvents (benzene and carbon disulfide) in these reactions. In the dealkylation reaction, the change of counter-ion from halogens to tetrafluoroborate had a dramatic effect on the stereo selectivity, showing the importance of the counter-ion in the course of the reactions. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4375 / 4377

页数：3

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