The condensation of α-chlorophenylacetonitrile (1) with benzaldehyde (2) carried out in the presence of 50% aq. NaOH and a quaternary ammonium catalyst gives trans-2,3-diphenylglycidonitrile, while without the catalyst, the cis-isomer predominates; in the latter case the reaction proceeds at the interface.
A. Jończyk, A. Kwast and M. Makosza, J. Chem. Soc., Chem. Commun., 1977, 902 DOI: 10.1039/C39770000902
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