The site-selectivity of cycloadditions of nitrile oxides to β-aminocinnamonitriles. A remarkable solvent dependence

Cycloadditions of nitrile oxides to N-mono and unsubstituted β-aminocinnamonitriles are remarkably affected by the hydrogen acceptor ability of the solvent. Addition to C ? N bond predominates in non and weak hydrogen bond acceptor solvents because of the assistance of favourable hydrogen bonding effects. In strong hydrogen bond acceptor solvents the assistance is fully relieved and the regular addition to C ? C bond becomes prevalent.