Strathprints logo
Strathprints Home | Open Access | Browse | Search | User area | Copyright | Help | Library Home | SUPrimo

Sodium-mediated magnesiation of thiophene and tetrahydrothiophene: structural contrasts with furan and tetrahydrofuran

Blair, V.L. and Kennedy, A.R. and Mulvey, R.E. and O'Hara, C.T. and , EPSRC (Funder) (2010) Sodium-mediated magnesiation of thiophene and tetrahydrothiophene: structural contrasts with furan and tetrahydrofuran. Chemistry - A European Journal, 16 (29). pp. 8600-8604. ISSN 0947-6539

[img]
Preview
PDF (strathprints028043.pdf)
Download (385Kb) | Preview

    Abstract

    Sulfur-containing heterocycles are currently attracting a great deal of interest in several diverse fields. For instance, substituted tetrahydrothiophenes[1] have received considerable attention due to their extremely wide-ranging chemical and biological applications.[2] These include their use as potent a-glucosidase inhibitors,[3] as an inhibitor of copper amine oxidases[4] and as selective A3 agonists and antagonists.[5] In addition, they have been utilised in chemical transformations, such as catalytic asymmetric epoxidation, catalytic intramolecular cyclopropanation, and asymmetric metal catalysis hydrogenation.[6] From a nanochemical perspective, the adsorption chemistries and physical properties of various thiophenes and tetrahydrothiophenes on gold surfaces have recently come to the fore.[7] Polythiophenes are also key compounds in modern materials research, currently utilised in, for example, the fabrication of semi-conducting, fluorescent, and electronic and optoelectronic materials.[8]In this work, metallation (exchange of a hydrogen atom with a metal atom) of the parent heterocycles, tetrahydrothiophene (THT) and thiophene is considered. Metallation is one of the most fundamental reactions in modern day synthesis and is a key tool in the preparation of functionalised aromatic and heterocyclic compounds. It is usually achieved by the utilisation of commercially accessible organolithiums (or lithium amides); however, these reactions do have their drawbacks, including the intolerance of certain functional groups, the need for cryoscopic temperatures and the inadvertent reactivity with polar reaction solvents.

    Item type: Article
    ID code: 28043
    Keywords: magnesiation, thiophene, tetrahydrothiophene, furan, tetrahydrofuran, Chemistry, Chemistry(all)
    Subjects: Science > Chemistry
    Department: Faculty of Science > Pure and Applied Chemistry
    Related URLs:
    Depositing user: Dr Charles Thomas O'Hara
    Date Deposited: 03 Nov 2010 11:34
    Last modified: 27 Mar 2014 11:23
    URI: http://strathprints.strath.ac.uk/id/eprint/28043

    Actions (login required)

    View Item

    Fulltext Downloads: