Easy and Selective Method for the Synthesis of Various Mono-O-functionahzed Calix[4]arenes: De-O-functionalization Using TiCl4

被引：11

作者：

Bois, Joackim ^{[2
]}

Espinas, Jeff ^{[1
,2
]}

Darbost, Ulrich ^{[2
]}

Felix, Caroline ^{[2
]}

Duchamp, Christian ^{[2
]}

Bouchu, Denis ^{[2
]}

Taoufik, Mostafa ^{[1
]}

Bonnamour, Isabelle ^{[2
]}

机构：

[1] Univ Lyon 1, C2P2, CNRS CPE Lyon, UMR 5265, F-69616 Villeurbanne, France

[2] Univ Lyon 1, CNRS, Equipe CSAp, Inst Chim & Biochim Mol & Supramol,UMR 5246, F-69622 Villeurbanne, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 22期

关键词：

REGIOSELECTIVE SYNTHESIS; COMPLEXATION; CALIXARENES; DERIVATIVES; RIM;

D O I：

10.1021/jo101319s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and selective method for the monofunctionalization of p-tert-butylcalix[4]arene is described A mono-de-O-functionalization of disubstituted p-tert-butylcalix[4]arenes using titanium tetrachloride was developed to synthesize a series of monosubstituted p-tert-butylcalix[4]arenes with the pendant functions being ethoxycarbonylmethyloxy, 3-ethoxycarbonylpropyloxy, cyanomethyloxy, 3-cyanopropyloxy, 4-bromobutyloxy, 3-hydroxypropyloxy, propyloxy, 2-methylpropyloxy, 3-butynyloxy, and 3-cyanopropyloxy groups The reaction mechanism of the formation of 5,11,17,23-tetra-tert-butyl-26,27,28-trihydroxy-25-(3-ethoxycarbonylpropyloxy) calix[4]arene was studied by H-1 NMR and GC/mass spectroscopy monitoring Reaction of TiCl4 with the disubstituted p-tert-butylcalix[4]arene produced the corresponding dioxocalix[4]arene titanium dichloride complex, which undergoes elimination of ethyl 4-chlorobutyrate, leading to a trioxocalix[4]arene titanium dichloride complex and to monosubstituted calix[4]arene after hydrolysis These two complexes were also synthesized, isolated, and fully characterized

引用

页码：7550 / 7558

页数：9

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