Anion Radical [2 + 2] Cycloaddition as a Mechanistic Probe:  Stoichiometry- and Concentration-Dependent Partitioning of Electron-Transfer and Alkylation Pathways in the Reaction of the Gilman Reagent Me2CuLi·LiI with Bis(enones)

• Published in: Journal of organic chemistry Vol. 69; no. 23; pp. 7979 - 7984
• Main Authors: Yang, Jingkui, Cauble, David F, Berro, Adam J, Bauld, Nathan L, Krische, Michael J
• Format: Journal Article
• Language: English
• Published: American Chemical Society 12.11.2004

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...