Sparing the ortho-position in nucleophilic aromatic substitution-specific displacement of the 4-SePh group in 2,4-bis(phenylseleno)nitrobenzene

Nicolai Stuhr-Hansen, Thorstein Finn Götze, Lars Henriksen, Theis Ivan Sølling, Annette Langkilde, Henning Osholm Sørensen

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    Upon treatment of o- and p(phenylseleno,)nitrobenzenes with sodium methoxide quantitative exchange reactions took place, affording the corresponding methoxynitrobenzenes. Upon reaction between 2,4-bis(phenylseleno)nitrobenzene 2 and sodium methoxide, an unusual regiopure formation of 4-methoxy-2-(phenylseleno)nitrobenzene 3 was observed. This product remained unreactive toward an excess of sodium methoxide, thus preventing the for-mation of 2,4-dimethoxynitrobenzene 6. The nature of the reactants and of the intermediate Meisenheimer complexes was examined by synthetic investigations, x-ray crystallography, and DFT calculations. We found that the observed selectivity can be understood in terms of traditional resonance considerations. (C) 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:101-108, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20519
    Original languageEnglish
    JournalHeteroatom Chemistry
    Volume20
    Issue number2
    Pages (from-to)101-108
    ISSN1042-7163
    DOIs
    Publication statusPublished - 2009

    Keywords

    • Materials characterization and modelling
    • Materials research

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