Synthesis of functionalized cavity structures via 1,3-dipolar cycloaddition of angle-shaped alkenes to curved norbornene-framed dipoles
(Equation Presented) A new approach to the synthesis of cavity molecules is described in which the 1,3-dipolar ACE coupling method is used to join curved-frame spacer molecules with obtuse-angled alkenes. The curved-frame spacers are comprised of fused norbornenes in which each alternative bridge has the 7-methylene replaced by oxygen. Molecular modeling (AM1) has been used to evaluate the geometry of a selection of bis-crown ether systems, the largest of which has nine norbornane units in the frame, a separation of 20.7 Å and the walls of the cavity having an interplanar angle of 36°.
Warrener, R., Margetic, D., Amarasekara, A., & Russell, R. (1999). Synthesis of functionalized cavity structures via 1,3-dipolar cycloaddition of angle-shaped alkenes to curved norbornene-framed dipoles. Retrieved from https://digitalcommons.pvamu.edu/chemistry-physics-facpubs/115