Reactions of nitrosalicylic aldehydes with chloromethyl tolyl sulfone anion. Synthesis of 2-hydroxydihydrobenzofurans.

摘要

Vicarious nucleophilic substitution of hydrogen (VNS) with chloromethyl tolyl sulfone carbanion does not occur in 3-, 4- and 5-nitrosalicylaldehydes. Instead, nucleophilic addition to the carbonyl group takes place leading to 2-hydroxydihydrobenzofurans. The same reaction course is observed for other salicyl aldehyde derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved. [References: 13]