Abstract
This paper reports original results concerning the Se/Li exchange reaction involving the cleavage of the C-Se bond of aryl alkyl selenides by butyllithiums. This reaction is one of the methods available to produce functionalized organolithium compounds.
Highlights
We report some specific examples which delineate the scope and limitation of the seleniumlithium exchange reaction between alkyllithiums and a series of alkyl phenyl selenides, producing dialkyl selenides and aryllithiums
We have compared the reactivity of a series of alkyl phenyl selenides and alkyllithiums whose tetragonal carbon attached to the selenium or/and the lithium atom is increasingly substituted by alkyl groups
We have compared the aptitude of alkyllithiums to cleave chemoselectively the C-Se bond of a series of butyl aryl selenides whose phenyl group is substituted by electron withdrawing or releasing groups
Summary
Organolithium compounds, the "Gilman reagents", have found wide application in organic synthesis.1a-g They are accessible, possess a wide range of reactivity which at several occasions surpass that of their organomagnesium competitors, the "Grignard reagents".2 They are more reactive, possess a greater aptitude (i) to perform metallation reactions (hydrogen/lithium exchange) (ii) to add to unactivated C,C double bonds and (iii) to add 1,2 to enones.1h. Organolithium compounds, the "Gilman reagents", have found wide application in organic synthesis.1a-g They are accessible, possess a wide range of reactivity which at several occasions surpass that of their organomagnesium competitors, the "Grignard reagents".2 They are more reactive, possess a greater aptitude (i) to perform metallation reactions (hydrogen/lithium exchange) (ii) to add to unactivated C,C double bonds and (iii) to add 1,2 to enones.1h. We report in this paper our detailed work on the synthesis of aryllithium compounds from related selenides which involve the selenium/lithium (Se/ Li)-exchange reaction This reaction, first reported by Gilman on phenyl methyl selenide and n-butyllithium was found to proceed quite sluggishly in refluxing ether. In many cases reported above, the selenium/lithium exchange proved to be the only method available to produce organolithiums and in the case of allyl- and benzyllithiums the method of choice for their synthesis
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