Issue 0, 1980

1,3-Dipolar character of six-membered aromatic rings. Part 52. 2π+ 8π Cycloaddition reactions of 1-substituted 3-oxidopyridinium betaines

Abstract

Dichloroketen and a series of aryl(bromo)ketens react with various 1-substituted 3-oxidopyridiniums to give novel bicyclic compounds by addition across the C(4)–O and the C(2)–O positions. Frontier-MO theory is used to rationalise the orientation of these cycloadditions. Acid-catalysed hydrolysis of the C(2)–O adducts (9) yielded 3-hydroxy-2-benzylpyridines.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1980, 1176-1184

1,3-Dipolar character of six-membered aromatic rings. Part 52. 2π+ 8π Cycloaddition reactions of 1-substituted 3-oxidopyridinium betaines

A. R. Katritzky, A. T. Cutler, N. Dennis, G. J. Sabongi, S. Rahimi-Rastgoo, G. W. Fischer and I. J. Fletcher, J. Chem. Soc., Perkin Trans. 1, 1980, 1176 DOI: 10.1039/P19800001176

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