Anodic oxidation of unsaturated α-stannyl ethers in Bu4NClO4âCH2Br2 results in effective cyclization and the introduction of bromide into one of the original olefinic carbons; a mechanism involving the coupling between the cyclized carbocation and Brâ generated by cathodic reduction of CH2Br2 is suggested.
Redox selective reactions of organo-silicon and -tin compounds
作者:Jun-ichi Yoshida、Keiji Nishiwaki
DOI:10.1039/a803343i
日期:——
The C-Si and C-Sn sigma orbitals are higher in energy than C-H or C-C sigma orbitals, and therefore can interact with neighboring pi systems, non-bonding orbitals of heteroatoms, and other sigma systems such as those of C-Si and C-Sn, Such interactions cause an increase of the HOMO level which in turn favors electron transfer. On the basis of this effect various types of redox selective reactions of organo-silicon and -tin compounds have been developed.
Yoshida, Jun-Ichi; Ishichi, Yuji; Isoe, Sachihiko, Journal of the American Chemical Society, 1992, vol. 114, # 19, p. 7594 - 7595