SET Oxidation Reactions of R2C=SiRLi

Daniel Pinchuk, Chemistry, Technion, Haifa, Israel
Jomon Mathew, Chemistry, Technion, Haifa, Israel
Boris Tumanskii , Chemistry, Technion, Haifa, Israel
Dmitry Bravo-Zhivotovskii, Chemistry, Technion, Haifa, Israel
Yitzhak Apeloig, Chemistry, Technion, Haifa, Israel

The reaction of 1 with different substituted bromobenzenes was studied. Reaction of 1 with bromobenzene or iodobenzene yields the phenyl substituted silene 2 (Scheme, path a). In contrast, with the sterically hindered 1-bromo-2,4,6-tri-tert-butylbenzene the unknown silenyl radical 3 was observed and characterized by EPR spectroscopy (Scheme, path b). Reaction of 1 with MesBr yields the unknown bromosilene 4 characterized by NMR spectroscopy (Scheme, path c).