Spirodienone derivatives of a spherand-type calixarene

K. Agbaria, O. Aleksiuk, S. E. Biali*, V. Böhmer, M. Frings, I. Thondorf

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations


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 C1 and C3 symmetries, respectively. The same tris(spirodienone) products were obtained by oxidation of 9 with I2/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.

Original languageAmerican English
Pages (from-to)2891-2899
Number of pages9
JournalJournal of Organic Chemistry
Issue number9
StatePublished - 4 May 2001


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