Issue 6, 1990

The alkaline stability of (5Z)-7-([2RS,4RS,5SR]-4-o-hydroxyphenyl-2-trifluoromethyl-1,3-dioxan-5-yl)hept-5-enoic acid, ICI 185282. A remarkable intramolecular hydride transfer from a trifluoromethyl substituted carbon atom

Abstract

The kinetics of hydrolysis of (5Z)-7-([2RS,4RS,5SR]-4-o-hydroxyphenyl-2-trifluoromethyl-1,3-dioxan-5-yl)hept-5-enoic acid, ICI 185282 (1a), have been studied. At low pH the compound undergoes conventional acid-catalysed hydrolysis of the dioxane ring. However, under alkaline conditions, a second reaction is observed. Studies by NMR show that this process involves a quite unexpected intramolecular hydride transfer from a carbon atom carrying a strongly electronwithdrawing trifluoromethyl substituent. Additional studies on closely related compounds are reported and a mechanism involving a ring-opened quinone methide intermediate is proposed.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1990, 965-970

The alkaline stability of (5Z)-7-([2RS,4RS,5SR]-4-o-hydroxyphenyl-2-trifluoromethyl-1,3-dioxan-5-yl)hept-5-enoic acid, ICI 185282. A remarkable intramolecular hydride transfer from a trifluoromethyl substituted carbon atom

J. L. Longridge and S. Nicholson, J. Chem. Soc., Perkin Trans. 2, 1990, 965 DOI: 10.1039/P29900000965

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements