- Molecular Rearrangements. XXVI. Thermolysis and Photolysis of Arenesulphohydroxamic Acids
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Thermolysis of arenesulphohydroxamic acid (Ar=Ph or p-tolyl) by heating at its melting point in air for 10 min gave nitric oxide, sulphurdioxide, and ammonia together with the corresponding arene, biaryl, diaryl sulphide, diaryl disulphide, diaryl sulphone, diaryl disulphone, thiophenol, aryl ammonium sulphonate, arene sulphonic acid and ammonium sulphite.Similar results were obtained on photolysis in acetone solution for 20 h at room temperature.The photolysis was found to be an intramolecular process as shown by cross-over experiment.A free-radical mechanism starting by homolysis of the S-N bond was suggested to account for the observed results.
- Aly, M. M.,Fahmy, A. M.,Abdel-Latif, F. F.,Badr, M. Z. A.
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- Synthesis of Benzoquinazoline-2,4-diones via Lossen Rearrangement of N-(Arylsulphonyloxy)naphthalene-2,3-dicarboximide Derivatives
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Treatment of N-(arylsulphonyloxy)-1-phenylnaphthalene-2,3-dicarboximides (IIa, b) with ammonia, aromatic amines, amino acids and hydrazine hydrate brings about the imide ring opening followed by Lossen rearrangement to give benzoquinazoline-2,4-diones (IIIa-h) and the salts of arylsulphonic acids (IVa-p).
- Hamed, A. A.,El-Bieh, A. A.,Baddawy, H. A.,Metwally, R. N.
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p. 221 - 223
(2007/10/02)
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