Regioselective Grafting of Two -CH2P(X)Ph2 Units (X = O, Lone Pair) onto a Resorcin[4]arene-Derived Cavitand

• Published in: European Journal of Organic Chemistry Vol. 2010; no. 6; pp. 1158 - 1168
• Main Authors: El Moll, Hani, Sémeril, David, Matt, Dominique, Toupet, Loïc
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.02.2010; WILEY‐VCH Verlag; Wiley-VCH
• Subjects: Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Cavitands; Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Phosphane oxides; Phos­phanes; Preparations and properties; Resorcinarene; Ruthenium; Terpenoids; Phosphane oxides; Ligand; Resorcinarene; Cavitands; Selectivity; Oxygen heterocycle; Grafting; Phosphorus Organic compounds; Macrocycle; Cavitand; Tertiary phosphine oxide; Functionalization; Cymene; Bromine Organic compounds; Aromatic compound; Phosphanes; Cyclophane; Chemical synthesis; Terpenoid; Arene; Ruthenium; Regioselectivity; Organic phosphine; Steric hindrance; Calixarene; X ray diffraction; Dinuclear complex; Monoterpene; Inclusion compound
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200901201

The first diphosphanes based on a resorcinarene‐derived cavitand were obtained in six steps starting from 5,11,17,23‐tetrabromo‐4(24),6(10),12(16),18(22)‐tetramethylenedioxy‐2,8,14,20‐tetrapentylresorcin[4]arene. The synthesis of these bulky ligands was based on the selective C‐2 functionalisation either of two proximal resorcinolic units or of two distal ones. The ligands, both of which were characterised by X‐ray diffraction, readily react with [RuCl2(p‐cymene)]2 to form the corresponding bimetallic complexes [RuCl2(p‐cymene)]2·L in which the cavitand shape remains unchanged with respect to that of the free phosphanes. The first diphosphanes based on a resorcinarene cavitand were conveniently prepared in six steps from a tetrabrominated precursor. The new ligands were shown tobe suitable for the preparation of bimetallic complexes without alteration of the shape of the generic cavitand core.