0000000000699595

AUTHOR

And Rossella Mello

showing 2 related works from this author

Iodomethane Oxidation by Dimethyldioxirane:  A New Route to Hypoiodous Acid and Iodohydrines

1999

The oxidation of iodomethane with dimethyldioxirane allows the generation of stable neutral solutions of hypoiodous acid in the absence of any trapping agent for iodide anion. Hypoiodous acid is trapped in situ by addition to representative olefins to give iodohydrines in good yields. The stereochemical study of the products shows the anti-stereospecific nature of the iodohydroxylation reaction.

chemistry.chemical_classificationchemistry.chemical_compoundchemistryOrganic ChemistryIodideOrganic chemistryPhysical and Theoretical ChemistryDimethyldioxiranePhotochemistryBiochemistryHypoiodous acidOrganic Letters
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Oxyfunctionalization of Aliphatic Esters by Methyl(trifluoromethyl)dioxirane

1996

The oxidation of lineal, cyclic, and bicyclic aliphatic p-chlorobenzoic and p-chorobenzenesulfonic acid esters 2 with methyl(trifluoromethyl)dioxirane (TFDO) (1) occurs at positions in the hydrocarbon chain distant from the directing group with a significant degree of selectivity to give the corresponding keto or hydroxy esters. Compounds 2 are relatively deactivated with respect to this oxidation due to the electron-withdrawing nature of the ester moiety. Methylene Cα−H and Cβ−H bonds remain unchanged in all cases, but tertiary Cβ−H bonds undergo oxidation with TFDO (1). Stereoelectronic factors are used to explain the faster reaction rate in competition experiments for the oxidation of en…

chemistry.chemical_classificationReaction ratechemistry.chemical_compoundTrifluoromethylHydrocarbonchemistryDioxiraneBicyclic moleculeOrganic ChemistryMoietyMethyleneSelectivityMedicinal chemistryThe Journal of Organic Chemistry
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