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Investigation of the acid catalysed Diels-Alder reactions of furan derivatives

Prokesova, M. and Toma, S. and Kennedy, A.R. and Knox, G.R. (1999) Investigation of the acid catalysed Diels-Alder reactions of furan derivatives. Tetrahedron, 54 (31). pp. 9175-9186. ISSN 0040-4020

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Abstract

Attempts have been made on trifluoroacelJc acid catalysed Diels-Alder reaction of furan, 2,5-dimethylfuran and 2,5-diphenylfuran with ,8-ferroccnyl-a-enones. No Diels-Alder products were isolated or detected but products from the FriedeI-Crafls fl-alkylation of furan ring were prepared in some cases. Reaction with 1,3-diphenylbenzo[c]furan under the same conditions resulted in the formation of a formal [4+3 ] cycioaddition product containing 1,2-disubstituted ferrocene.