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Journal of Organic Chemistry | 2010

Easy and selective method for the synthesis of various mono-O-functionalized calix[4]arenes: de-O-functionalization using TiCl4.

Joackim Bois; Jeff Espinas; Ulrich Darbost; Caroline Felix; Christian Duchamp; Denis Bouchu; Mostafa Taoufik; Isabelle Bonnamour

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 (1)H 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.


Transition Metal Chemistry | 2016

Synthesis and crystal structures of palladium(II) complexes of bis-(N-heterocyclic carbenes) on a calix[4]arene platform

Hui Ren; Benjamin Ourri; Erwann Jeanneau; Tao Tu; Isabelle Bonnamour; Ulrich Darbost

A series of calix[4]arene supported N-heterocyclic carbene palladium complexes were successfully prepared and characterised. Their X-ray crystal structures were obtained and are discussed. Notably, the dimeric compound b[5-(3-N-4,5-diphenylimidazol-2-yliden-1-yl)-25,26,27,28-tetrapropyloxy calix[4]arene] palladium(II) dibromide (cone) showed pseudo-polymorphism.


Separation and Purification Technology | 2007

Selective thiacalix[4]arene bearing three amide groups as ionophore of binary Pd(II) and Au(III) extraction by a supported liquid membrane system

Asma Zaghbani; Rafik Tayeb; Mahmoud Dhahbi; Manuela Hidalgo; Francis Vocanson; Isabelle Bonnamour; Patrick Seta; Clàudia Fontàs


Tetrahedron | 2014

Synthesis, characterization and X-ray structures of N-heterocyclic carbene palladium complexes based on calix[4]arenes: highly efficient catalysts towards Suzuki–Miyaura cross-coupling reactions

Hui Ren; Yong Xu; Erwann Jeanneau; Isabelle Bonnamour; Tao Tu; Ulrich Darbost


European Journal of Inorganic Chemistry | 2010

Titanacalixarenes in Homogeneous Catalysis: Synthesis, Conformation and Catalytic Activity in Ethylene Polymerisation

Jeff Espinas; Ulrich Darbost; Jeremie Pelletier; Erwan Jeanneau; Christian Duchamp; François Bayard; Olivier Boyron; Jean-Pierre Broyer; Jean Thivolle-Cazat; Jean-Marie Basset; Mostafa Taoufik; Isabelle Bonnamour


Organometallics | 2011

Synthesis of Novel Tantalacalixarene Complexes: First Example of Intramolecular CH Activation of Monodepleted Aromatic Ring

Jeff Espinas; Jérémie D. A. Pelletier; Erwan Jeanneau; Ulrich Darbost; Kai C. Szeto; Christine Lucas; Jean Thivolle-Cazat; Christian Duchamp; Natali Henriques; Denis Bouchu; Jean-Marie Basset; Henry Chermette; Isabelle Bonnamour; Mostafa Taoufik


Tetrahedron Letters | 2012

Synthesis and characterization of a stable copper (I) calix(4)dicyano-diimidazole complex

Sébastien Noël; Hui Ren; Tao Tu; Erwann Jeanneau; Caroline Felix; Florent Perret; Francis Vocanson; Christophe Bucher; Guy Royal; Isabelle Bonnamour; Ulrich Darbost


Tetrahedron Letters | 2012

Synthesis, characterization, and conformational analysis of new perfunctionalized calix[9]arenes

Mouna Ferchichi; Erwann Jeanneau; Bernard Fenet; Faouzi Meganem; Ulrich Darbost; Isabelle Bonnamour


Chem | 2011

The First Inexpensive, Simplified and Large Scale Synthesis of p-tert-butylcalix[7] and [9]arenes

Mouna Ferchichi; Erwann Jeanneau; Jean-Claude Sollier; Faouzi Meganem; Ulrich Darbost; Isabelle Bonnamour


European Journal of Inorganic Chemistry | 2010

Titanacalixarenes in Homogeneous Catalysis: Synthesis, Conformation and Catalytic Activity in Ethylene Polymerisation (Eur. J. Inorg. Chem. 9/2010)

Jeff Espinas; Ulrich Darbost; Jeremie Pelletier; Erwan Jeanneau; Christian Duchamp; François Bayard; Olivier Boyron; Jean-Pierre Broyer; Jean Thivolle-Cazat; Jean-Marie Basset; Mostafa Taoufik; Isabelle Bonnamour

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