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Issue 2, 2011
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A water-soluble phosphite derived from sulfonated calix[4]arene. The remarkable stability of its rhodium complexes and two phase hydroformylation studies

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Abstract

The reaction of tetrasulfonated calix[4]arene (trioctylammonium salt) with P(NMe2)3 followed by treatment with gaseous NMe2H gave a zwitterionic six-coordinate phosphorus(V) species 1 containing a P(H)(NHMe2) group which can be stored for months without decomposition. In water, 1 loses NHMe2 and rearranges to form the water soluble phosphite Lcc. Phosphite Lcc has a half-life in water of ca. 5 h decomposing to H3PO3 and free tetrasulfonated calix[4]arene. Compound 1 serves as a convenient precursor to Lcc and complexes of Lcc are formed by dissolving 1 in water in the presence of labile metal complexes. The products have been identified by comparison of their 31P NMR data with well established analogues of calix[4]arene derived phosphites. In this way the water soluble complexes [Rh(acac)(CO)(Lcc)2] (2c) [Rh2Cl2(CO)2(Lcc)2] (3c), [Pt2Cl4(Lcc)2] (4c) and [PtCl2(Lcc)2] have been tentatively identified. The rhodium complex 3c has a half-life in water of 4 months. Two-phase (water/toluene) hydroformylation of 2-methylpentenoate with 2c as a catalyst has been investigated and the results compared with the same reaction in toluene with lipophilic analogues of 2c. Under mild conditions, with 2ccatalyst, branched aldehydes are the only products of hydroformylation and one of the branched aldehydes is selectively hydrogenated to give the lactone derivative.

Graphical abstract: A water-soluble phosphite derived from sulfonated calix[4]arene. The remarkable stability of its rhodium complexes and two phase hydroformylation studies

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Publication details

The article was received on 28 Oct 2010, accepted on 14 Dec 2010 and first published on 10 Feb 2011


Article type: Paper
DOI: 10.1039/C0CY00031K
Citation: Catal. Sci. Technol., 2011,1, 239-242
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    A water-soluble phosphite derived from sulfonated calix[4]arene. The remarkable stability of its rhodium complexes and two phase hydroformylation studies

    C. J. Cobley and P. G. Pringle, Catal. Sci. Technol., 2011, 1, 239
    DOI: 10.1039/C0CY00031K

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