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Novel Reactions Of Donor-Acceptor Cyclopropanes, And Diels-Alder Approach Towards Fargesine And Fumimycin, Polydoros Kyriacou

Electronic Thesis and Dissertation Repository

The first chapter of this thesis consists of two related projects that explore novel reactivity of donor-acceptor cyclopropanes, specifically 2-substituted cyclopropane 1,1-diesters. The first project involves the nucleophilic ring opening of donor-acceptor cyclopropanes with potassium organotrifluoroborates. It was found that during the ring opening of the cyclopropane, the diesters of the cyclopropane formed a malonyl-BF₂ complex. The complex could then be hydrolyzed to afford substituted malonates. The reaction was limited to aryl cyclopropanes and potassium alkynyltrifluoroborates. The second project in this chapter explores modifying the Kerr group’s previous synthesis of tetrahydro-1,2-oxazines, such that geminal allyl, methyl esters are now …