Formation of Grignard Reagents from Aryl Halides:  Effective Radical Probes Hint at a Nonparticipation of Dianions in the Mechanism

Autor: Bodineau, N., Mattalia, J.-M., Thimokhin, V., Handoo, K., Negrel, J.-C., Chanon, M.
Zdroj: Organic Letters; July 2000, Vol. 2 Issue: 15 p2303-2306, 4p
Abstrakt: We have prepared highly efficient radical probes 2ab involving the hex-5-enyl rearrangement. The reaction of 2ab with active magnesium leads to the cyclized products 4ab, providing a direct evidence of radical intermediates during the formation of aryl Grignard reagents. The variations of yields for cyclized products 4ab as a function of structural modifications in 2ab suggest that the intervention of dianions is not necessary to explain the observed results.
Databáze: Supplemental Index