Selenides, acetamido

Chiral acetamido selenides 147, obtained from alkenes with camphorselenenyl sulfate, underwent intramolecular substitution in the presence of PhSeOTf or SO2CI2 to afford enantiomerically pure oxazolines 148 <00EJO3451>. 

The same reaction, but in the presence of triflic acid, results in /i-acetamido selenides by a mv-addition. In the case of a terminal olefin, the phenylseleno group is introduced mainly at the terminal carbon atom.13... 

Direct anodic oxidation of PhSeSePh at a Pt anode in MeCN-Bu4NBF4 containing alkenes results in 2-acetamido selenides in good yields [61]. 

Acetamido selenides, easily prepared from olefins, undergo regioselective oxidative elimination to give high yields of allylic amides e.g. Scheme 54). ... 

Several papers have appeared describing the cleavage of disulphides and diselenides with phosphines. A two-step mechanism applies to the reduction of a disulphide with Ph3P in aqueous media, and the intermediate Ph3PSAr ArS hydrolyses to ArSH + PhaPO. More complex disulphides containing acetamido-alkyl and o a-di(ethoxycarbonyl)alkyl substituents give oxazole and trisulphide side-products during reduction with PhaP. Conversion of dimethyl diselenide with (R2N)aP into dimethyl selenide, and photochemical deselenation of diethyl diselenide to diethyl selenide with PhaPMe, which involves an EtSe radical chain mechanism, have been described. 

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