Synthesis of Functionalized Cavity Structures via 1,3-Dipolar Cycloaddition of Angle-Shaped Alkenes to Curved Norbornene-Framed Dipoles

Synthesis of Functionalized Cavity Structures via 1,3-Dipolar Cycloaddition of Angle-Shaped Alkenes to Curved Norbornene-Framed Dipoles

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 rep...

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Bibliographic Details
Published in:Organic letters Vol. 1; no. 2; pp. 203 - 206
Main Authors: Warrener, Ronald N, Margetic, Davor, Amarasekara, Ananda S, Russell, Richard A
Format: Journal Article
Language:English
Published: American Chemical Society 29-07-1999
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Summary: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°.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol990538d