Tetrahedron

The vicarious nucleophilic substitution of hydrogen and related reactions in nitrobenzoxazoles

M Ma̧kosza, J Stalewski

Index: Makosza, Mieczyslaw; Stalewski, Jacek Tetrahedron, 1995 , vol. 51, # 26 p. 7277 - 7286

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Citation Number: 10

Abstract

5-and 6-nitrobenzoxazoles 3 and 4 react with nucleophiles exclusively at C-2, giving ring opening products. If position 2-is blocked with phenyl substituent the reaction takes place in the carbocyclic ring affording the VNS products. 2-Methylthio-5-nitrobenzoxazole 7 and its 6- nitro isomer 8 give products which result from addition of a nucleophile to the carbocyclic ring (VNS) as well as to the heterocyclic ring (SNAr and ring cleavage). 2- ...