Favorable effect of ortho substituents on selenoxide syn elimination of n-alkyl aryl selenoxides
n-Alkyl aryl selenides with an ortho substituent were found to be superior to the corresponding para isomers as starting materials for the preparation of terminal olefins when hydrogen peroxide was used as the oxidant, because the para isomers afforded unwanted selenones and a primary alcohol as by-products. (C) 2000 Elsevier Science Ltd.
Sayama, Shinsei,Onami, Tetsuo
p. 5557 - 5560
(2007/10/03)
173.Ru-Catalyzed Oxidations with Iodosylbenzene Derivatives. Substituent Effects on Selectivity in Oxidation of Sulfides and Alcohols
Oxidation of sulfides witth PhIO/RuCl2(PPh3) leads to sulfones.Electronwithdrawing substituents in the aromatic ring of PhIO reduce the reactivity and improves selectivity of the system.Thus, with m-iodosylbenzoic acid sulfides are converted to sulfoxide.Under the same conditions aliphatic primary alcohols are transformed to aldehydes with m-iodosylbenzoic acid, while PhIO affords carboxylic acids.
Mueller, Paul,Godoy, Jose
p. 1790 - 1796
(2007/10/02)
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