Reaction of (–)-menthyl(S)-toluene-p-sulphinate with nitriles and lithium NN-di-isopropylamide (LDA) in 1:1:1 and 1:2:1 ratios affords optically active α-cyano- and α-cyano-β-imino-sulphoxides, respectively. α-Cyanobenzyl sulphoxide racemizes through a homolytic process in a temperature range (35–50 °C) well below that required for benzyl aryl sulphoxides.
R. Annunziata, M. Cinquini, S. Colonna and F. Cozzi, J. Chem. Soc., Perkin Trans. 1, 1981, 614 DOI: 10.1039/P19810000614
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