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Substituent effects in hydroxyiodination of 1,2-diacyloxycyclohex-3-enes

Sweeney, Joseph B., Knight, J.R. and Thobhani, Smita (2006) Substituent effects in hydroxyiodination of 1,2-diacyloxycyclohex-3-enes. Tetrahedron, 62 (50). pp. 11565-11571. ISSN 0040-4020

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Abstract

The reaction of 1,2-diacyloxycyclohex-3-enes with iodinating agents in the presence of water has been investigated. The process is inherently diastereoselective, with many reactions giving only two of the four possible diastereoisomers which could be obtained. However, the regiocontrol is variable: highest selectivities are observed when pivalates are present on the periphery of the cycloalkene, when single regio- and diastereoisomers are obtained from the reactions.

Item Type: Article
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
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Depositing User: Joseph Sweeney
Date Deposited: 18 Oct 2012 12:23
Last Modified: 18 Oct 2012 12:23
URI: http://eprints.hud.ac.uk/id/eprint/15221

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