Spirodienone derivatives of a spherand-type calixarene

被引：10

作者：

Agbaria, K ^{[1
]}

Aleksiuk, O

Biali, SE

Böhmer, V

Frings, M

Thondorf, I

机构：

[1] Hebrew Univ Jerusalem, Dept Organ Chem, IL-91904 Jerusalem, Israel

[2] Johannes Gutenberg Univ Mainz, Abt Lehramt Chem, Fachbereich Chem & Pharm, D-55099 Mainz, Germany

[3] Univ Halle Wittenberg, Fachbereich Biochem Biotechnol, Inst Biochem, D-06099 Halle, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 09期

关键词：

D O I：

10.1021/jo001648x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2891 / 2899

页数：9

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