A study of some molecularly imprinted polymers as protic catalysts for the isomerisation of α-pinene oxide to trans-carveol

  • Motherwell W
  • Bingham M
  • Pothier J
 et al. 
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A range of acidic Molecularly Imprinted Polymers (MIPs) were synthesised using the imprint molecule trans-carvyl amine as a transition state analogue for the selective isomerisation of α-pinene oxide to trans-carveol. The amine functionality of the imprint molecule was used to selectively position a sulfonic acid group in the MIP binding pocket utilising 4-styrene sulfonic acid as the functional monomer. Co-polymerisation with varying ratios of styrene and divinylbenzene afforded a range of MIPs which were tested for their ability to effect selective formation of trans-carveol from α-pinene oxide. Although successful imprinting was demonstrated in binding studies, it was shown that solvent effects were dominant in effecting selective formation of trans-carveol. Using DMF as solvent, up to 70% of the products from acid catalysed isomerisation of α-pinene oxide with the polystyrene MIPs were obtained via the necessary para menthyl tertiary carbocation, and industrially important trans-carveol was obtained in 45% yield. © 2004 Elsevier Ltd. All rights reserved.

Author-supplied keywords

  • Molecularly imprinted polymers
  • Trans-Carveol
  • α-Pinene oxide

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  • William B. Motherwell

  • Matilda J. Bingham

  • Julien Pothier

  • Yvan Six

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