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Report | Regular issue | Vol 19, No. 1, 1982, pp.57-66
Published online, 1st January, 1970
DOI: 10.3987/R-1982-01-0057
Regioselectivity of Reactions of 2-Furoyl-N-aryl Nitrile Imine with Some Dipolarophiles

Ahmad Sami Shawali, Hamdi Mahmoud Hassaneen, Abdel-Fattah Shetta, Abdou Osman, and Fathi Abdel-Galil

*Department of Chemistry, Faculty of Science, University of Cairo, Giza, Egypt


The regioselectivity of the cycloadditions of nitrile imines (1a-d), derived from 2-furoylhydrazidoyl chlorides (3a-d), to the C=C and C=S double bonds of the enol tautomer of acetylacetone 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 7 is on the carbon atom.