| Abstract: | The regioselectivity of the cycloadditions of α,β-unsaturated nitrilimine derived from N-phenylcinnamo-hydrazidoyl chloride 2 to C = Se, C = S and C = C double bonds of the resonance stabilized selenocyanate and thiocyanate anions, enol tautomer of dibenzoylmethane and benzalacetophenone was investigated. The results indicate that the reactions studied are dipole-LUMO-dipolarophile-HOMO controlled and that the larger orbital coefficient in the LUMO of N-phenylcinnamonitrilimine is on the carbon atom bearing the styryl group. The structures of the cycloadducts were assigned and confirmed on the basis of their elemental analyses and spectra. |
