Gorichko M. Interaction of bromosubstituted camphor derivatives with nucleophilic reagents

The thesis is devoted to chemistry of functionalized cage compounds, namely, reactions of bromosubstituted camphor derivatives with nucleophiles. It was established that the outcome of this interaction depends on the number and spatial arrangement of the bromo substituents, and on the nature of the nucleophilic reagents. Direct substitution, formation of the 4-oxatricyclo[4.3.0.03,7]nonane derivatives, nucleophilic rearrangements, and intramolecular alkylation of enolates were observed.Direct substitution observed with sterically not demanding nucleophiles like thiolate ions. The camphor derivatives with bromo-substituent in 8-th position usually form 4-oxatricyclo[4.3.0.03,7]nonane derivatives, although alkylation of corresponding enolates occurred rapidly in the case if nucleophiles are strong bases. Other bromoderivatives of camphor underwent nucleophilic rearrangements.