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


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2015-04

AUTHORS

Nenad Maraš, Marijan Kočevar

ABSTRACT

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. More... »

PAGES

697-704

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s00706-014-1383-6

DOI

http://dx.doi.org/10.1007/s00706-014-1383-6

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1009189233


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59 schema:description 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.
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