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  • Lithium Bromide, an Inexpensive and Efficient Catalyst for Opening of Epoxide Rings by Amines at Room Temperature under Solvent-Free Condition

    Author(s)
    Chakraborti, AK
    Rudrawar, S
    Kondaskar, A
    Griffith University Author(s)
    Rudrawar, Santosh
    Year published
    2004
    Metadata
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    Abstract
    Lithium bromide has been found to be an inexpensive and efficient catalyst for the opening of epoxide rings by amines, and this provides an environmentally friendly method for the synthesis of β‐amino alcohols. Aromatic and aliphatic amines react with cycloalkene oxides to exclusively form trans‐2‐(aryl/alkylamino)cycloalkanols in high yields. A 98−100% selectivity in favour of nucleophilic attack at the benzylic carbon atom of styrene oxide is observed with aromatic amines. However, aliphatic amines exhibit a marginal preference for the reaction at the terminal carbon atom of the epoxide ring in styrene oxide. Non‐styrenoidal, ...
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    Lithium bromide has been found to be an inexpensive and efficient catalyst for the opening of epoxide rings by amines, and this provides an environmentally friendly method for the synthesis of β‐amino alcohols. Aromatic and aliphatic amines react with cycloalkene oxides to exclusively form trans‐2‐(aryl/alkylamino)cycloalkanols in high yields. A 98−100% selectivity in favour of nucleophilic attack at the benzylic carbon atom of styrene oxide is observed with aromatic amines. However, aliphatic amines exhibit a marginal preference for the reaction at the terminal carbon atom of the epoxide ring in styrene oxide. Non‐styrenoidal, unsymmetrical alkene oxides undergo selective nucleophilic attack at the sterically less hindered carbon atom by aniline. The chelation effect of the Li+ ion enables selective opening of the epoxide ring in 3‐phenoxypropylene oxide in the presence of styrene oxide.
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    Journal Title
    European Journal of Organic Chemistry
    Volume
    2004
    Issue
    17
    DOI
    https://doi.org/10.1002/ejoc.200400253
    Subject
    Medicinal and biomolecular chemistry
    Biologically active molecules
    Organic chemistry
    Publication URI
    http://hdl.handle.net/10072/100282
    Collection
    • Journal articles

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