Phenyliodoso acetate

Ketones can be a hydroxylated in good yields, without conversion to the enolates, by treatment with the hypervalent iodine reagents162 o-iodosobenzoic acid163 or phenyliodoso acetate PhI(OAc)2 in methanolic NaOH.164 The latter reagent has also been used on carboxylic esters.165 02 and a chiral phase transfer catalyst gave enantioselective a hydroxylation of ketones, if the a position was tertiary.166... 

Oxidation of arylmethyl ketoximes by phenyliodoso diacetate in glacial acetic acid was second order overall, first order each in substrate and oxidant.145 Iodine allowed the oxidative dimerization of glycine ester enolates with low to moderate diastereoselec-tivity that is consistent with kinetic control.146 Although malonic acid is not oxidized by iodate under acidic conditions, oxidation proceeds in the presence of catalytic ruthenium(III). A mechanism is put forward to account for the observed orders of reaction.147 The rate of periodate oxidation of m-toluidine in acetone-water increases with ionic strength.148... 

Lead and Phenyliodoso Azides. When lead(TV) acetate and phenyliodoso derivatives are used as a catalyst for azidation of alkenic and aromatic compounds (eq 11), lead azides and phenyliodoso azides are formed as intermediates. 

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