The formation and isolation of benzisothiazole rings from the reactions of oxime-thiophenolate ligands

Fierro, C.M., Murphy, B.P., Smith, P.D., Coles, S.J. and Hursthouse, M.B. (2006) The formation and isolation of benzisothiazole rings from the reactions of oxime-thiophenolate ligands. Inorganica Chimica Acta, 359, (7), 2321-2327. (doi:10.1016/j.ica.2005.11.047).


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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.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1016/j.ica.2005.11.047
ISSNs: 0020-1693 (print)
Related URLs:
Keywords: berizisothiazole, n-oxo benzisothiazole, nickel(ii)-thiolate, schiff-base, crystal structure copper(ii) complexes, thiolate complexes, nickel(ii), fe, hydrogenase, tsalen, ni, cu
Subjects: Q Science
Q Science > QD Chemistry
Divisions : University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 44438
Accepted Date and Publication Date:
Date Deposited: 02 Mar 2007
Last Modified: 31 Mar 2016 12:18

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