143033-66-3Relevant articles and documents
Reactions of Squaric Acid with Phenylhydrazine: Structure and Nuclear Magnetic Resonance Spectroscopy of Cyclobutanetetraone Poly(phenylhydrazones)
Khadem, Hassan S. El,Shalaby, M. Ashraf,Coxon, Bruce,Fatiadi, Alexander J.
, p. 1511 - 1518 (2007/10/02)
The reaction of squaric acid 1 with phenylhydrazine affords three cyclobutanetetraone poly(phenylhydrazones), viz. a tetrakis(phenylhydrazone) 3, a tris(phenylhydrazone) 4a 4b 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 andN,N-diphenyl analogues 8 and 9 from cyclobutanetetraone, and the preparation of a quinoxaline 7 to establish the 1,3-arrangement of substituents.