Electrophilic aromatic substitution with N-methoxy-N-acylnitrenium ions generated from N-chloro-N-methoxy amides: syntheses of nitrogen heterocyclic compounds …

M Kawase, T Kitamura, Y Kikugawa

Index: Kawase, Masami; Kitamura, Takahiro; Kikugawa, Yasuo Journal of Organic Chemistry, 1989 , vol. 54, # 14 p. 3394 - 3403

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Citation Number: 117

Abstract

N-Methoxy-N-acylnitrenium ions (11), generated by treatment of N-chloro-N-methoxyamides with silver carbonate in trifluoroacetic acid, react with arenes to give N-aryl-N- methoxyamides in good yields. In the case of the intramolecular cyclization of N-chloro-N- methoxy-2-phenylacetamides, the mode of cyclization is highly dependent on the nature of ortho or para substituent groups. Nitrenium ions I1 can primarily attack three positions (C- ...