REAL

The cis-trans isomerisation of homologous 2-hydroxycycloalkanecarboxylic acids under basic conditions

Gyarmati, Cs. Zsuzsanna and Pálinkó, István and Bokros, Attila and Martinek, A. Tamás and Bernáth, Gábor (2006) The cis-trans isomerisation of homologous 2-hydroxycycloalkanecarboxylic acids under basic conditions. CHINESE JOURNAL OF CHEMISTRY, 24. pp. 1792-1795. ISSN 1001-604X

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Abstract

The cis-->trans isomerisation of homologous 2-hydroxycycloalkanecarboxylic acids in strongly basic aqueous solution was studied starting from the cis isomers. It was found that the cyclopentane, cyclohexane and cycloheptane homologues afforded synthetically useful amounts of the trans acids and the procedure resulted in relatively small quantities of the corresponding olefinic acids. In contrast, the isomerisation of the cis-2-hydroxycyclooctanecarboxylic acid produced roughly equal amounts of the cis and trans isomers and the 1-cyclooctenecarboxylic acid at equilibrium. Molecular modelling with the PM3 semiempirical method of the reactants, products and the intermediates applying explicit water molecules as reaction medium gave a fair estimate for the rate sequence of the idealised (dehydration-free) isomerisation reactions in aqueous base solution.

Item Type: Article
Subjects: Q Science / természettudomány > QD Chemistry / kémia
SWORD Depositor: MTMT SWORD
Depositing User: MTMT SWORD
Date Deposited: 31 May 2013 11:24
Last Modified: 31 May 2013 11:24
URI: http://real.mtak.hu/id/eprint/5423

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