Abstract

A rapid and highly selective chlorination method has been developedusing 2,4,6-trichloro-1,3,5-triazine (TCT) catalyzed by dimethylsulfoxide. The reactions take 10 to 40 minutes, and the yields arealmost quantitative. The neutral reaction conditions are compatiblewith substrates bearing acid-labile functional groups. Both competitiveintramolecular and intermolecular reactions for benzyl alcoholsin the presence of aliphatic alcohols indicate high selectivity.The procedure has been successfully used in the selective chlorinationof gastrodin, a clinically used neuromedicine. This procedure representsa useful new tool in organic and medicinal chemistry.

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