Issue 12, 1992

Reactions of squaric acid with phenylhydrazine: structure and nuclear magnetic resonance spectroscopy of cyclobutanetetraone poly(phenylhydrazones)

Abstract

The reaction of squaric acid 1 with phenythydrazine affords three Cyclobutanetetraone poly(phenylhydrazones), viz. a tetrakis(phenylhydrazone)3, a tris(phenylhydrazone)4a4b and a 1,3-bis(phenylhydrazone)5. The structure of these compounds has been determined by IR, MS and 1H and 13C NMR spectroscopy, including 2D COSY, and 1H-detected, single- and multiple-bond 2D carbon–proton chemical-shift-correlation techniques. Chemical methods were also used to elucidate the structure of bis(phenylhydrazone)5, including its synthesis and that of its N-methyl-N-phenyl and N,N-diphenyl analogues 8 and 9 from cyclobutanetetraone, and the preparation of a quinoxaline 7 to establish the 1,3-arrangement of substituents.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1992, 1511-1517

Reactions of squaric acid with phenylhydrazine: structure and nuclear magnetic resonance spectroscopy of cyclobutanetetraone poly(phenylhydrazones)

H. S. El Khadem, M. A. Shalaby, B. Coxon and A. J. Fatiadi, J. Chem. Soc., Perkin Trans. 1, 1992, 1511 DOI: 10.1039/P19920001511

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