Shizheng Zhu
Feb 1, 1994
Citations
0
Influential Citations
24
Citations
Journal
Heteroatom Chemistry
Abstract
Phenyliodonium bis(perfluoroalkanesulfonyl) methides PhI+−C(SO2RF)2 (3) were prepared by the reaction of bis(perfluoroalkanesulfonyl)methanes with diacetoxyiodobenzene. The photochemical reactions of 3 with alkenes, methanol, bromine, and benzene gave the corresponding addition or insertion products. When 3 was irradiated in the presence of methyl sulfide, pyridine, and triphenylphosphine, it afforded the ylides containing the bis(perfluoroalkanesulfonyl)methylene functionality, Y+−C(SO2RF)2. In these reactions the bis(perfluoroalkanesulfonyl)carbene intermediate (RFSO2)2C: may be involved. Irradiation or heating of 3 in DMSO gave a 1 : 1 complex, the structure of which was confirmed by X-ray diffraction analysis. Bis(perfluoroalkanesulfonyl)-methylene dimethyloxosulfonium ylides Me2(O)S+−C(SO2RF)2 were obtained by air oxidation of bis(perfluoroalkanesulfonyl)methylene dimethylsulfonium ylides.