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Paper | Special issue | Vol 58, No. 1, 2002, pp.183-190
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(M)7
Diels-Alder Cycloaddition of Highly Substituted Pyran-2-ones with Maleic Anhydride

Kristof Kranjc, Ivan Leban, Slovenko Polanc, and Marijan Kočevar*

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, P.O. Box 537, SLO-1000 Ljubljana, Slovenia


The Diels-Alder cycloaddition reaction of substituted 3-benzoylamino-pyran-2-ones (1) with maleic anhydride (2) in 1,2,3,4-tetrahydronaphthalene yielding representatives of bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetra-carboxylic acid 2,3;5,6-dianhydride (5) has been investigated. The emphasis was given both on the study of the influence of substituents on the reaction and development of the synthesis of derivatives with unprecedented substituent patterns. Structures of products were determined by the X-Ray study and by the spectroscopic analyses.