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Issue 23, 2002
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Phosphine containing dendrimers for highly regioselective rhodium catalysed hydroformylation of alkenes: a positive ‘dendritic effect’

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Abstract

Diphenylphosphine functionalised polyhedral oligomeric silsesquioxane (POSS) dendrimers are used as ligands for the rhodium catalysed hydroformylation of oct-1-ene showing unexpectedly high regioselectivity to the linear aldehyde nonan-1-al (l ∶ b = 14 ∶ 1). Comparative studies with the small molecule analogues, bis-diphenylphosphinopentane, Me2Si[CH2CH2PPh2]2 and Si[CH2CH2PPh2]4, clearly confirm the unusual selectivity of these bidentate dendritic ligands and show that a ‘positive dendritic effect’ occurs. This high selectivity is obtained with only one structure within the 1st and 2nd generation dendrimer (spacer of five atoms between the phosphorus atoms, and carbon–silicon linkage) whilst other frameworks (spacer of three and seven atoms between the P atoms, or carbon–oxygen–silicon linkage) lead to lower selectivity.

Graphical abstract: Phosphine containing dendrimers for highly regioselective rhodium catalysed hydroformylation of alkenes: a positive ‘dendritic effect’

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Publication details

The article was received on 08 Jul 2002, accepted on 04 Sep 2002 and first published on 01 Nov 2002


Article type: Paper
DOI: 10.1039/B206597E
Citation: J. Chem. Soc., Dalton Trans., 2002,0, 4323-4334
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    Phosphine containing dendrimers for highly regioselective rhodium catalysed hydroformylation of alkenes: a positive ‘dendritic effect’

    L. Ropartz, K. J. Haxton, D. F. Foster, R. E. Morris, A. M. Z. Slawin and D. J. Cole-Hamilton, J. Chem. Soc., Dalton Trans., 2002, 0, 4323
    DOI: 10.1039/B206597E

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