Tetrahedron Letters

Radical intermediates in the Zn-promoted Barbier-type alkylation of diphenyl diselenide in aqueous medium

JAL dos Anjos, LW Bieber

文献索引：Dos Anjos, Jose Ayron Lira; Bieber, Lothar Wilhelm Tetrahedron Letters, 2012 , vol. 53, # 48 p. 6492 - 6494,3

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被引用次数: 3

摘要

The zinc promoted Barbier-type reaction of alkyl halides and diphenyl diselenide in aqueous medium leads to high yields of mixed selenides even in acidic medium. Especially the efficient formation of t-butylphenylselenide cannot be explained by nucleophilic substitution and raises the question of an alternative reaction mechanism. Three suitable halide precursors of 'radical clocks' of increasing rate of unimolecular rearrangement were used ...