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An organoiron approach to thyroid hormone analogues
Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
2005 (English)In: Journal of Organo metallic Chemistry, Vol. 690, 1784-1792 p.Article in journal (Refereed) Published
Abstract [en]

An approach to thyroid hormone analogues was proposed involving sequential substitution of cationic cyclopentadienyl(1.4-dichlorobenzene)iron(II) complexes with phenoxide/thiophenoxide and hydroxide/amine, followed by decomplexation. Although the selectivity for monosubstitution with phenolates and thiophenolates was poorer than previously observed, it was often possible to control the reaction with sterically less demanding phenolates of intermediate nucleophilicity. The subsequent introduction of a polar substituent into the monosubstituted product was successful with amine nucleophiles. A modified approach, based on the reverse order of substitution was also attempted. Whereas clean monosubstitution with hydroxide/hydroxide equivalents was unsuccessful, cyclopentadienyl(N-alkyl-1-chloro-4-aminobenzene)iron(II) complexes could be prepared in fair yields and further substituted with nucleophiles such as thiophenolates.

Place, publisher, year, edition, pages
2005. Vol. 690, 1784-1792 p.
Keyword [en]
Thyroid hormones, (1, 4-Dichlorobenzene)iron(II) complexes, Sequential substitution, Phenoxide/thiophenoxide, Hydroxide/amine
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-70578DOI: doi:10.1016/j.jorganchem.2005.01.032OAI: oai:DiVA.org:uu-70578DiVA: diva2:98489
Available from: 2005-04-25 Created: 2005-04-25 Last updated: 2011-01-12

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Engman, Lars

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