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Exo-Stereoselective 1,3-Dipolar Cycloadditions of Nitrile Oxides to Endo-7-(R1,R2- methylene)bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylates

V. Ondruš, Ľ. Fišera, P. Ertl, and N. Prónayová

Department of Organic Chemistry, Faculty of Chemical Technology, Slovak Technical University, SK-812 37 Bratislava


Abstract: 1,3-Dipolar cycloaddition of arylnitrile oxides to endo-N-(3,5-dichlorophenyl)imide 7-R1,R2- methylene)bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylates (R1,R2= phenyl, methyl, 2-thienyl, 2-furyl) led exclusively to endo-exo cycloadducts. Semiempirical quantum-mechanical methods AMI showed that the exclusive exo-1,3-dipolar cycloaddition can be rationalized through the secondary orbital interaction between 1,3-dipole and π orbital of the exo-cyclic C=C double bond in the methylene bridge. Both endo-syn-exo and ende-anti-exo cycloadducts were formed in the ratio 50 : 50 in the case of R1≠R2.

Full paper in Portable Document Format: 486a399.pdf


Chemical Papers 48 (6) 399–403 (1994)

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