The formation and isolation of benzisothiazole rings from the reactions of oxime-thiophenolate ligands |
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| Authors: | Claudio Mendicute Fierro Paul D. Smith Simon J. Coles |
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| Affiliation: | a Department of Chemistry and Materials, Manchester Metropolitan University, Manchester M1 5GD, UK
b Department of Chemistry, EPSRC National Crystallography Service, University of Southampton, Highfield, Southampton SO17 1BJ, UK |
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| Abstract: | The reaction of [Ni(eftp)] [eftp = N,N-ethylene(6-formyl-4-methyliminatothiophenolato)] with hydroxylamine hydrochloride in the presence of potassium acetate in MeOH resulted in the formation of [Ni(L)2], L = 2-mercapto-5-methyl-3-({2-[(5-methyl-benzo[d]isothiazol-7-ylmethylene)-amino]-ethylimino}-methyl)-benzonitrile. A single-crystal X-ray diffraction structural determination showed that the oxime groups of the proposed new binucleating ligand had reacted to produce a nitrile and an isothiazole ring, while two ligand molecules combined with one Ni(II) ion to form a new complex with a cis-S2N2 square-planar geometry. Also, the reaction of 2,6-diformyl-4-methylphenyl disulfide with hydroxylamine in MeCN resulted in the synthesis of 5-methyl-2-oxy-benzo[d]isothiazole-7-carbaldehyde oxime, where an isothiazole ring had formed via the cleavage of the disulfide bond. Again, a single-crystal X-ray diffraction study confirmed the presence of a benzisothiazole product. |
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| Keywords: | Benzisothiazole N-oxo benzisothiazole Nickel(II)-thiolate Schiff-base Crystal structure |
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