60990-44-5Relevant articles and documents
Fenton-Inspired C-H Functionalization: Peroxide-Directed C-H Thioetherification
Groendyke, Brian J.,Modak, Atanu,Cook, Silas P.
, p. 13073 - 13091 (2019)
Substoichiometric iron mediates the thioetherification of unactivated aliphatic C-H bonds directed by resident silylperoxides. Upon exposure to a catalytic amount of iron(II) triflate, TIPS-protected peroxides bearing primary, secondary, and tertiary C-H sites undergo chemoselective thioetherification of remote C-H bonds with diaryl disulfides. The reaction demonstrates a broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic experiments suggest that the reaction proceeds through 1,5-H atom abstraction by a hydroxyl radical generated with iron.
Intramolecular Addition of Alkoxy Radicals. Part 4. Reductive Cyclisation of Olefinic Hydroperoxides
Taillez, Bernard,Bertrand, Michele Paula,Surzur, Jean-Marie
, p. 547 - 554 (2007/10/02)
Pent-4-enyl hydroperoxide reacts with reducing salts (FeX2, TiCl3) to afford tetrahydrofurfuryl compounds (halides or dimers) in high yield from the selective cyclisation of the pent-4-enyloxy radical.Analogous behaviour is observed for photolysis although the yields of cyclic products are lower.The photolysis of hex-5-enyl hydroperoxide does not yield cyclic products but these are observed when this hydroperoxide is reduced by FeCl2.It is suggested that metallic salts are able to complex the alkoxyl radicals thereby making them more electrophilic and hence more prone to cyclise.
