PMID: 11325250Apr 28, 2001Paper

Spirodienone derivatives of a spherand-type calixarene

The Journal of Organic Chemistry
K AgbariaI Thondorf

Abstract

Oxidation of the spherand-type calixarene 4 with 1 or 2 equiv of phenyltrimethylammonium tribromide/base afforded mono- and bis(spirodienone) derivatives (8b and 9, respectively). The spirodienone groups are derived from the oxidation of two phenols connected by a common methylene group. NOESY data indicated that 9 possesses a "head to tail" arrangement of the spirodienone groups. Oxidation of 4 with 3 equiv of the oxidizing reagent afforded two tris(spirodienone) calixarene derivatives 11 and 10 with C(1) and C(3) symmetries, respectively. The same tris(spirodienone) products were obtained by oxidation of 9 with I(2)/aq KOH. Tris(spirodienone) 11 displayed NOE cross-peaks in the NOESY NMR spectrum consistent with a nonalternant disposition of carbonyl and ether groups. Upon heating 10 and 11 isomerize in the solid state and in solution. The major component in the equilibration mixtures is 11, indicating that this is the thermodynamically more stable tris(spirodienone) isomer.

References

Apr 28, 2001·The Journal of Organic Chemistry·K AgbariaI Thondorf

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Citations

Mar 8, 2019·Chemical Communications : Chem Comm·Hans-Jörg Schneider
Dec 31, 2008·Organic Letters·Francesco TroisiPlacido Neri
Dec 14, 2001·Journal of the American Chemical Society·K Agbaria, S E Biali
Aug 4, 2001·The Journal of Organic Chemistry·K Agbaria, S E Biali

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