Hydrolysis of Cyclopentenyl-alkyl-N-methyl Nicotinates in Micelles and Cyclodextrines

Abstract

The formation, via superstructures of a high selectivity was obtained through the ionic interaction, electronic charge-transfer interaction, hydrophobic interaction, and van der Waals interaction in the hydrolysis of iodide-2-(Δ³-cyclopentenyl)-ethyl-N-methyl-nicotinate, 12, and iodide-3-(Δ³-cyclopenthenyl)-propyl-N-methyl-nicotinate, 14, in micelles and cyclodextrins. Hydrolysis was accomplished in the aqueous solutions of α- and β-cyclodextrins (CD) and in the aqueous solutions of cetyltrimethylammonium bromide (CTAB). The choice of the leaving group (nicotinate) and the reaction medium influence the reaction rate and the composition of the formed products. Contrary to published data, the hydrolysis of iodide-2-(Δ³-cyclopenthenyl)-ethyl-N-methyl-nicotinate, 12, in the presence of α-CD yielded endo-2-norborneol.

Keywords:

• Hydrolysis
• Cyclopentenyl-alkyl-nicotinates
• Cyclodextrins
• Micelles
• Selectivity

Acknowledgements

This work was supported by a grant from the Ministry of Science, Education and Sports No. 1-07-185.