Issue 7, 2000
From the journal:

Journal of the Chemical Society, Dalton Transactions

Calix[4]arene based monophosphites, identification of three conformations and their use in the rhodium-catalysed hydroformylation of 1-octene

Floris J. Parlevliet,a   Christoph Kiener,a   Jan Fraanje,b   Kees Goubitz,b   Martin Lutz,c   Anthony L. Spek,c   Paul C. J. Kamera  and  Piet W. N. M. van Leeuwen*a  

* Corresponding authors

a Department of Inorganic Chemistry and Homogeneous Catalysis, Institute of Molecular Chemistry, University of Amsterdam, The Netherlands
E-mail: pwnm@anorg.chem.uva.nl

b Department of Crystallography, Institute of Molecular Chemistry, University of Amsterdam, The Netherlands

c Department of Crystal and Structural Chemistry, Bijvoet center for Biomolecular Research, University of Utrecht, The Netherlands

Abstract

Eight monodentate phosphites (2–9) based on the calix[4]arene backbone were synthesised following two synthetic routes. Out of six conformations only three were actually formed under the applied reaction conditions. X-Ray analysis of two conformers (4 and 5) provided insight into the 3-dimensional structure of two of these conformations. The three conformations were characterised by 1H, 13C and 31P NMR spectroscopy. NMR experiments showed that several of the phosphites are flexible showing fluxional behaviour of the molecular backbone in solution, but no interconversion between the different conformers was observed. The conformation of the product in the phosphite synthesis is determined at the point where the phosphorus atom is linked to two hydroxyl groups of the calix[4]arene (phosphorus amidite). Such an intermediate phosphorus amidite (12) was isolated in the synthesis of 4 and 5. Phosphites 3–6, 8 and 9 were tested in rhodium-catalysed hydroformylation. Differences in rate can be correlated to the conformation of the ligand.

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Article information

DOI
https://doi.org/10.1039/A909103C
Article type
Paper
Submitted
17 Nov 1999
Accepted
01 Feb 2000
First published
17 Mar 2000

J. Chem. Soc., Dalton Trans., 2000, 1113-1122

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Calix[4]arene based monophosphites, identification of three conformations and their use in the rhodium-catalysed hydroformylation of 1-octene

F. J. Parlevliet, C. Kiener, J. Fraanje, K. Goubitz, M. Lutz, A. L. Spek, P. C. J. Kamer and P. W. N. M. van Leeuwen, J. Chem. Soc., Dalton Trans., 2000, 1113 DOI: 10.1039/A909103C

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