The regioselectivity of the cyloadditions of nitrile imines 1, derived from Aryl Carbamoyl hyd- razidoyl chlorides 2, to the C=C and C=S double bonds of the enol tautomer of benzoyl aceta- nilide, ethyl benzoylacetate, p-acetoacetotoluidide and the resonance stabilized thiocyanate anion respectively was investigated. The results indicate that the reactions studied are dipole- LUMO controlled and that the larger orbital coefficient in the LUMO of 1 is on the carbon atom.