Anion Radical [2+ 2] Cycloaddition as a Mechanistic Probe: Stoichiometry-and Concentration-Dependent Partitioning of Electron-Transfer and Alkylation Pathways in …

…, AJ Berro, NL Bauld, MJ Krische

Index: Yang, Jingkui; Felton, Greg A. N.; Bauld, Nathan L.; Krische, Michael J. Journal of the American Chemical Society, 2004 , vol. 126, # 6 p. 1634 - 1635

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Citation Number: 32

Abstract

Exposure of easily reduced aromatic bis (enones) 1a-1e to the methyl Gilman reagent Me2CuLi⊙ LiI at 0° C in tetrahydrofuran solvent provides the products of tandem conjugate addition-Michael cyclization, 2a-2e, along with the products of [2+ 2] cycloaddition, 3a-3e. Complete partitioning of the Gilman alkylation and [2+ 2] cycloaddition pathways may be achieved by adjusting the loading of the Gilman reagent, the rate of addition of the Gilman ...