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Naji, M. |
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Motta, Antonella |
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Aletan, Dirar |
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Mohamed, Tarek |
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Ertürk, Emre |
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Taccardi, Nicola |
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Kononenko, Denys |
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Petrov, R. H. | Madrid |
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Alshaaer, Mazen | Brussels |
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Bih, L. |
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Casati, R. |
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Muller, Hermance |
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Kočí, Jan | Prague |
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Šuljagić, Marija |
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Kalteremidou, Kalliopi-Artemi | Brussels |
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Azam, Siraj |
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Ospanova, Alyiya |
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Blanpain, Bart |
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Ali, M. A. |
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Popa, V. |
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Rančić, M. |
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Ollier, Nadège |
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Azevedo, Nuno Monteiro |
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Landes, Michael |
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Rignanese, Gian-Marco |
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Fierro, C. M.
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article
The formation and isolation of benzisothiazole rings from the reactions of oxime-thiophenolate ligands
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-methylbenzo[d]isothiazol-7-ylmethylene)-am ino]-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 nitrite 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-oxybenzo[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.