The αβ-dibromides from o-cyano-trans-cinnamonitrile, the corresponding dicarboxamide and the two cis-amidenitriles are labile and readily undergo stereospecific elimination and/or cyclisation reactions with wate or base. In this way, the cis- and trans-isomers of 3-cyanomethylenephthalide and of α-bromo-o-cyano-cinnamonitrile have been obtained.
J. A. Elvidge and D. E. H. Jones, J. Chem. Soc. C, 1971, 2424 DOI: 10.1039/J39710002424
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