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Reference type: Journal
Authors: Motherwell WB, Bingham MJ, Pothier J, Six Y
Article Title: A study of some molecularly imprinted polymers as protic catalysts for the isomerisation of a-pinene oxide to trans-carveol.
Publication date: 2004
Journal: Tetrahedron
Volume: 60
Issue: (14)
Page numbers: 3231-3241.
DOI: 10.1016/j.tet.2004.02.016

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 alpha-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 alpha-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 alpha-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. (C) 2004 Elsevier Ltd. All rights reserved

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