Issue 0, 1984
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

N-alkoxy-N-acylnitrenium ions as possible intermediates in intramolecular aromatic substitution: novel formation of N-acyl-3,4-dihydro-1H-2,1-benzoxazines and N-acyl-4,5-dihydro-1H,3H-2.1-benzoxazepine

Stephen A. Glover,   André Goosen,   Cedric W. McCleland  and  Johan L. Schoonraad  

Abstract

N-Halogeno-N-alkoxyamides undergo intramolecular aromatic substitution by thermal- or Lewis acid-catalysed heterolysis of the nitrogen–halogen bond. N-Acyl-N-alkoxynitrenium ions are likely intermediates. N-Chloro-N-methoxybiphenyl-2-carboxamide (4) yields N-methoxyphenanthridone (11) quantitatively with AgBF4, while O-2-phenylethyl-N-chlorobenzohydroxamate (19) is converted in good yield into N-benzoyl-3,4-dihydro-1H-2,1-benzoxazine (21) with AgBF4, AgClO4, HgO, and Hg(OAc)2. N-Acetyl-3,4-dihydro-1H-2,1-benzoxazine (22) is formed similarly. O-3-Phenylpropyl-N-chlorobenzohydroxamate (23) cyclises to N-benzoyl-4,5-dihydro-1H,3H-2,1-benzoxazepine (24) with AgBF4.

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Article information

DOI
https://doi.org/10.1039/P19840002255
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1984, 2255-2260

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N-alkoxy-N-acylnitrenium ions as possible intermediates in intramolecular aromatic substitution: novel formation of N-acyl-3,4-dihydro-1H-2,1-benzoxazines and N-acyl-4,5-dihydro-1H,3H-2.1-benzoxazepine

S. A. Glover, A. Goosen, C. W. McCleland and J. L. Schoonraad, J. Chem. Soc., Perkin Trans. 1, 1984, 2255 DOI: 10.1039/P19840002255

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