Phenylseleninyl chloride

Phenylseleninyl chloride is also an efficient regio para- selective halogenating agent for activated aromatics such as phenol, phenol ethers and anilines958. Bis(4-chlorophenyl) selenide/Lewis acid mixtures chlorinate toluene preferentially at the para position959. Porphyrines are also chlorinated by PhSeCl and PhSeCl3960. PhSeBr brominates 3-keto steroids at the a-position961. 

Reich et al. have explored the use of phenylseleninyl chloride, CgHsSeOCl, m.p. 56-64°. This reagent can be prepared in 92% yield by ozonization of... 

OXIDATION, REAGENTS Acetyl nitrate. Bis(tri-n-butyltin)oxide. Bromine-Hexameth-ylphosphoric triamide. f-Butyl perbenzoate. Ceric ammonium nitrate. N-chlorosuc-cinimide-Dimethyl sulfide. Chromic add. Chromic anhydride. Chromic anhydride-Acetic anhydride. Chromic anhydride-Hexamethylphosphoric triamide. 2,3-Dichloro-5,6-dicyano-l,4-benzoquinone. Dimethyl sulfoxide. Dimethyl sulfoxide-Trifluoro-acetic anhydride. Diphenylseleninlc anhydride. Iodine tris(trifluoroacetate). Lead tetraacetate. N-Methylmorpholine -N-oxide. p-NitrobenzenesulfonyI peroxide. Oxygen, singlet. Palladlumfll) chloride. Peroxybcnzimidic acid. Phenylseleninyl chloride. N-Phenyl-l,2,4-triazoline-3,5-dione. Potassium chromate. Potassium superoxide. Pyri-dinium chlorodiromate. Salcomine. Silver carbonate-Celite. Sodium hypochlorite. Sulfuryl chloridc-Silica gel. Thallium(III) acetate. ThaUium(III) nitrate. Triphenyl phosphite ozonide. Trltyl tetrafluoroborate. Uranium hexafluoride. 

The role played by benzeneseleninic acid or by phenylseleninyl chloride in promoting the rearrangement of A-aryl-benzohydroxamic acids PhOONArOH to p-hydroxy-benzanilides relies on the formation of seleninate or selenenate esters, respectively, followed by Claisen-type shifts to ortho- and then para-positions. ... 

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