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

Autor: Maraš, Nenad, Kočevar, Marijan
Zdroj: Chemical Monthly / Monatshefte für Chemie; Apr2015, Vol. 146 Issue 4, p697-704, 8p
Abstrakt: 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. Graphical Abstract: [Figure not available: see fulltext.] [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index