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

Autor:	Julien Pothier, Matilda J. Bingham, Yvan Six, William B. Motherwell
Rok vydání:	2004
Předmět:	chemistry.chemical_classification Chemistry Organic Chemistry Molecularly imprinted polymer Oxide Sulfonic acid Divinylbenzene Biochemistry Styrene Solvent chemistry.chemical_compound Drug Discovery Organic chemistry Amine gas treating Solvent effects
Zdroj:	Tetrahedron. 60:3231-3241
ISSN:	0040-4020
DOI:	10.1016/j.tet.2004.02.016
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::954d69c668aaf916b4dc6a6eb5b73674 https://doi.org/10.1016/j.tet.2004.02.016 Zobrazit plný text záznamu Full Text from ScienceDirect