Several epoxides have been converted into Δ2-oxazolines by reaction with acetonitrile or benzonitrile in the presence of boron trifluoride–ether complex; yields are much higher than when reaction is brought about with sulphuric acid or tin(IV) chloride. The position of insertion of the nitrile and the stereochemistry of the ring enlargement are discussed.
J. R. L. Smith, R. O. C. Norman and M. R. Stillings, J. Chem. Soc., Perkin Trans. 1, 1975, 1200 DOI: 10.1039/P19750001200
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