The formation and isolation of benzisothiazole rings from the reactions of oxime-thiophenolate ligands
The formation and isolation of benzisothiazole rings from the reactions of oxime-thiophenolate ligands
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.
berizisothiazole, n-oxo benzisothiazole, nickel(ii)-thiolate, schiff-base, crystal structure
copper(ii) complexes, thiolate complexes, nickel(ii), fe, hydrogenase, tsalen, ni, cu
2321-2327
Fierro, C.M.
05e1d763-d926-4733-a0ce-655911740ea2
Murphy, B.P.
2e64bcaf-2526-44d7-87a4-ad1c3755c6c1
Smith, P.D.
5f720e42-d84d-4ef5-9547-eae324c2e8fa
Coles, S.J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, M.B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
2006
Fierro, C.M.
05e1d763-d926-4733-a0ce-655911740ea2
Murphy, B.P.
2e64bcaf-2526-44d7-87a4-ad1c3755c6c1
Smith, P.D.
5f720e42-d84d-4ef5-9547-eae324c2e8fa
Coles, S.J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, M.B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
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), .
(doi:10.1016/j.ica.2005.11.047).
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.
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Published date: 2006
Keywords:
berizisothiazole, n-oxo benzisothiazole, nickel(ii)-thiolate, schiff-base, crystal structure
copper(ii) complexes, thiolate complexes, nickel(ii), fe, hydrogenase, tsalen, ni, cu
Identifiers
Local EPrints ID: 44438
URI: http://eprints.soton.ac.uk/id/eprint/44438
ISSN: 0020-1693
PURE UUID: 9ebb9a73-29dd-4be1-be05-735992f33307
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Date deposited: 02 Mar 2007
Last modified: 16 Mar 2024 03:05
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Author:
C.M. Fierro
Author:
B.P. Murphy
Author:
P.D. Smith
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