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The diels-alder addition of dicyanoacetylene to [8] (2,5)furanophane; the synthesis of a paddlane

✍ Scribed by R. Helder; Hans Wynberg

Publisher
Elsevier Science
Year
1973
Tongue
French
Weight
210 KB
Volume
14
Category
Article
ISSN
0040-4039

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✦ Synopsis

Structures, that contain tetravalent carbon with the four neighbouring atoms in or close to a plane passing through this carbon ("planar carbon"), are intriguing to us from a prh+arative point of view.'

Calculations show that "planar carbon" will be thermodynamically less stable than tetrahedral carbon.:! The synthesis of the doubly-bridged structure 2 as described below was planned with the following idea in mind: a reversible reaction -the Diels-Alder additionmight enable us to establish the extent to which the "planarity" is possible. 3

Addition of [8 J(R,!j)furanophane (lj4 to an excess of dicyanoacetylene (DCA) at room temperature gave the Diels-Alder adduct 2 in 8~$ yield.

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