Preparation and Regioselective SN2‘ Reaction of Novel gem-Difluorinated Vinyloxiranes with RLi
The Journal of Organic Chemistry2004Vol. 69(22), pp. 7616–7627
Citations Over TimeTop 10% of 2004 papers
Abstract
A series of hitherto unknown 3,4-epoxy-1,1-difluorobutenes were prepared from the readily accessible alpha,beta-epoxy ketones and these compounds were found to undergo regioselective S(N)2' reactions with hard RLi nucleophiles occurring at the highly positively charged terminal fluorine-possessing sp(2) carbon atom in quite sharp contrast to the cases of the corresponding nonfluorinated vinyloxiranes which only attained a low level of regioselectivity. Addition of HMPA substantially improved the products' olefinic stereoselectivity. Theoretical calculations were used to qualitatively explore the nature of selectivity in these reactions.
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