Macrocyclic cyclophane belts via double Diels-Alder cycloadditions: Macroannulation of bisdienes by bisdienophiles. Synthesis of a key precursor to an [8]cyclacene

A synthesis of macrocyclic cyclophanes is accomplished by double Diels-Alder cycloaddition of two bisdienophiles, 1,4,5,8-anthradiquinone and p-phenylenedimaleimide, to a bisdiene, 2,3,6,7-tetraheptylidene-1,2,3,4,5,6,7,8-octahydroanthracene. The structure of the macrocyclic cyclophane derived from...

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Bibliographic Details
Published in:Tetrahedron letters 1996-03, Vol.37 (12), p.1983-1986
Main Authors: Cory, Robert M., McPhail, Cameron L., Dikmans, Antonius J., Vittal, Jagadese J.
Format: Article
Language:English
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Summary:A synthesis of macrocyclic cyclophanes is accomplished by double Diels-Alder cycloaddition of two bisdienophiles, 1,4,5,8-anthradiquinone and p-phenylenedimaleimide, to a bisdiene, 2,3,6,7-tetraheptylidene-1,2,3,4,5,6,7,8-octahydroanthracene. The structure of the macrocyclic cyclophane derived from the diquinone has been determined by single crystal x-ray diffraction, in addition to 1H and 13C NMR, HRMS and IR spectroscopic data. A synthesis of macrocyclic cyclophanes is accomplished by double Diels-Alder cycloaddition of two bisdienophiles, 1,4,5,8-anthradiquinone and p-phenylenedimaleimide, to a bisdiene, 2,3,6,7-tetraheptylidene-1,2,3,4,5,6,7,8-octahydroanthracene.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)00263-8