Synthesis of functionalized cavity structures via 1,3-dipolar cycloaddition of angle-shaped alkenes to curved norbornene-framed dipoles

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(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°.

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