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Unexpected Formation of Bisadducts in 1,3-Dipolar Cycloadditions to 7-(R1,R2-Methylene)bicyclo[2,2,1]hept- 2,5-diene-2,3-dicarboxylates

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

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


Abstract: The cycloaddition of arylnitrile oxides to dimethyl 7-(R1,R2-methylene)bicyclo[2,2,1]hept-2,5- diene-2,3-dicarboxylates proceeds under the formation of bisadducts and retroproducts. The other expected retroproducts were not formed. Semiempirical quantum-mechanical methods AM1 were used to rationalize this formation of bisadducts. The results are confronted with the siteselectivity of 7-oxabicyclo[2,2,1]hept-2,5-diene-2,3-dicarboxylate and dimethyl derivative of the title compound.

Full paper in Portable Document Format: 485a337.pdf


Chemical Papers 48 (5) 337–340 (1994)

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