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

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Abstract

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.

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Motherwell, W. B., Bingham, M. J., Pothier, J., & Six, Y. (2004). A study of some molecularly imprinted polymers as protic catalysts for the isomerisation of α-pinene oxide to trans-carveol. Tetrahedron, 60(14), 3231–3241. https://doi.org/10.1016/j.tet.2004.02.016

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