Oxidative Generation of Thioalkyl Cations from 2-Tributylstannyl-1,3-dithianes and 1-(Tributylstannyl)alkyl Sulfides and Their Reactions with Olefinic Nucleophiles
- 1 October 1993
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 66 (10) , 2995-3003
- https://doi.org/10.1246/bcsj.66.2995
Abstract
2-Tributylstannyl-1,3-dithianes and 1-(tributylstannyl)alkyl sulfides are oxidized with ammonium hexanitratocerate(IV) or ferrocenium hexafluorophosphate to generate their cation radicals, which dissociate into the carbocations and tributylstannyl radical. The carbocations thus generated react with olefinic nucleophiles to afford the corresponding addition products in good yield.This publication has 26 references indexed in Scilit:
- Electron-transfer oxidation of ketene silyl acetals and other organosilanes. Mechanistic insight into Lewis acid mediated electron transferJournal of the American Chemical Society, 1992
- Electron-transfer-induced photoadditions of the silyl amine, Et2NCH2SiMe3, to .alpha.,.beta.-unsaturated cyclohexenones. Dual reaction pathways based on ion pair-selective cation-radical chemistryJournal of the American Chemical Society, 1988
- A novel photosubstitution of dicyanobenzenes by allylic and benzylic silanesTetrahedron Letters, 1985
- Regioselective photoallylations of dicyanopolycyclic aromatic compounds via electron transferTetrahedron Letters, 1985
- Cation radical Diels-Alder reactions of electron-rich dienophilesJournal of the American Chemical Society, 1983
- Cation radicals. 48. Evidence for electron transfer in the alkylation of thianthrene cation radical with diethylmercuryThe Journal of Organic Chemistry, 1983
- Ion radicals. 43. Addition of thianthrene and phenoxathiin cation radicals to alkenes and alkynesThe Journal of Organic Chemistry, 1979
- Ion radicals. 39. Reactions of 10-methyl- and 10-phenylphenothiazine cation radical perchlorates with ketonesThe Journal of Organic Chemistry, 1977
- Ion radicals. XXXV. Reactions of thianthrene and phenoxathiin cation radicals with ketones. Formation and reactions of .beta.-ketosulfonium perchlorates and ylidesThe Journal of Organic Chemistry, 1975
- Ion radicals. XVIII. Reactions of thianthrenium perchlorate and thianthrenium trichlorodiiodideThe Journal of Organic Chemistry, 1969