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Article << Previous     |     Next >>   Contents Vol 50(4)

A Neutral Donor-Acceptor p-Stack: Solid-State Structures of 1 : 1 Pyromellitic Diimide-Dialkoxynaphthalene Cocrystals

Rina Carlini, Cheng-Lin Fang, Deborah Herrington, Kerianne Higgs, Russell Rodrigo and Nicholas Taylor

Australian Journal of Chemistry 50(4) 271 - 278
Published: 1997


Substituted ortho-benzoquinones, generated in situ by hypervalent iodine oxidation of catechols, are intercepted by unsymmetrical dienes to provide Diels-Alder adducts with complete regiospecificity. Catechols with carboxy substituents in the 3 or 4 positions react similarly and the initial adducts decarboxylate to produce 8-substituted or 5-substituted 1,2-dihydroxydihydronaphthalenes respectively, in a one-pot three-step sequence. The reaction has been further adapted to produce naphtho[1,8-bc]furans in a one-pot process; its application towards the synthesis of the tricyclic system of the sesquiterpene nardonoxide is described

Full text doi:10.1071/C96099

© CSIRO 1997

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