Effects of tertiary amine catalysis on the regioselectivity of anisole chlorination with trichloroisocyanuric acid

被引：4
作者：
Maras, Nenad [1 ]
Kocevar, Marijan [1 ]
机构：
[1] Univ Ljubljana, Fac Chem & Chem Technol, Ljubljana 1000, Slovenia
来源：
MONATSHEFTE FUR CHEMIE | 2015年 / 146卷 / 04期
关键词：
Chlorination; Catalysis; Electrophilic substitutions; Regioselectivity; DABCO; SELECTIVE AROMATIC CHLORINATION; QUATERNARY AMMONIUM-SALTS; N-CHLOROAMINES; SULFURYL CHLORIDE; ORGANIC-COMPOUNDS; MILD CONDITIONS; PHENOLS; HALOGENATION; BROMINATION; METHYLATION;
D O I：
10.1007/s00706-014-1383-6
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Tertiary amines and their salts in dichloromethane were found to induce a strong para regioselectivity in the chlorination of anisole as the model substrate with trichloroisocyanuric acid (TCCA). Using a catalyst loading of 6 mol % trimethylammonium chloride gave a para vs. ortho selectivity of 38:1. This effect is attributed to the in situ formation of N-chlorotrialkylammonium salts, which chlorinate alkyl aryl ethers with a high regioselectivity. The regioselectivity and monochlorination selectivity for anisole chlorination with TCCA in numerous solvents are reported. The chlorination of a few related benzenoid substrates under selected conditions is described.
引用
收藏
页码：697 / 704
页数：8
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