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    Sulfonic Acid Libraries Attained Through Opening of 2-Sulfobenzoic Acid Anhydride


    Robinson, Richard I. and Stephens, John C. and Worden, Steve M. and Blake, Alexander J. and Wilson, Claire and Woodward, Simon (2004) Sulfonic Acid Libraries Attained Through Opening of 2-Sulfobenzoic Acid Anhydride. European Journal of Organic Chemistry, 2004 (22). pp. 4596-4605. ISSN 1434-193X

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    Abstract

    2-Sulfobenzoic acid anhydride opens cleanly with N-Boc-protected α-amino alcohols to afford zwitterionic esters 1,2-C6H4(SO3−)(CO2CH2CHR1NH3+) (R1 = H, alkyl), the species R1 = iPr is crystallographically characterised. Dehydration of these species affords zwitterionic oxazoline sulfonic acid derivatives 1,2-C6H4(SO3−)(CA=NH+CHR1CH2OA) (CA and OA are bonded C−O) for R1 = iPr (X-ray), iBu, tBu, CH2Ph. Reaction with water regenerates the zwitterionic esters while exposure to M(OAc)2 (M = Cu, Pd) leads to the formation of the crystallographically characterised complexes MIIL2 (L = anion of the iPr-oxazolinesulfonic acid). Heating either the zwitterionic esters or oxazolines with R2NH2 [R2 = CH2Ph, CH2(1-C10H7), R-CH(Me)Ph] leads to SN2 attack at the oxazoline methylene group leading to the amido sulfonic acids 1,2-C6H4(CONHCHRCH2NHR2)(SO3H) based on crystallographic studies on R1 = iPr, R2 = CH2(1-C10H7).

    Item Type: Article
    Keywords: Molecular diversity; Amino alcohols; Sulfonic acids; S ligands; N,O ligands; Hydrogen bonding;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 7821
    Identification Number: https://doi.org/10.1002/ejoc.200400562
    Depositing User: Dr John Stephens
    Date Deposited: 27 Jan 2017 15:28
    Journal or Publication Title: European Journal of Organic Chemistry
    Publisher: Wiley
    Refereed: Yes
    Funders: European Commission
    URI:

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