Oxygenation vs iodonio substitution during the reactions of alkenyl-silanes with iodosylbenzene: participation of the internal oxy group.
Reaction of 4-acyl-oxy-but-1-enyl-silanes with iodosylbenzene in the presence of BF(3) x OEt(2) gave 4-acyloxy-2-oxobutyl-silane and 3-acyloxy-tetrahydrofuran-2-yl-silane via a 1,3-di-oxan-2-yl cation intermediate, which is generated by participation of the acyloxy group during the electrophilic addition of iodine(III) to the substrate.
Fujita
Morifumi
M
Graduate School of Material Science, Himeji Institute of Technology, University of Hyogo, 3-2-1 Kohto, Kamigori, Hyogo 678-1297, Japan. fuji@sci.u-hyogo.ac.jp
Lee
Hee Jin
HJ
Sugimura
Takashi
T
Okuyama
Tadashi
T