M-Chloropcrbcnzoic acid

BAEYER-VILLIGER OXIDATIONS Bis(trimethylsilyl)peroxide. m-Chloropcrbcnzoic acid, m-Chloroperbenzoic acid-Potassium fluoride. 

HYDROXY CARBOXYLIC ACIDS Dicyclohexylborane a -HY DROXY-a, [J-ENONES m-Chloropcrbcnzoic acid y-HYDROXY-a,B-ENONES Potassium peroxomonosulfate. a HYDROXY ESTERS Tris(phenylthio)methyllithium. a-HYDROXY-p-KETO ESTERS ... 

I) by oxidation with m-chloropcrbcnzoic acid, with 2 equivalents of lithium in liquid ammonia gives the alcohol (3) in 90% yield. In the same way, the epoxide (4) is converted into (5) in 95 % yield. In both cases (2) and (4) the cyclopropyl bond common to ihe two phenyl substiluents is ruptured with marked kinetic preference to give a radical anion, which is attacked by the proximate C-0 bond to form a new cyclopropane ring. The cyclopropane ring of (3) and of (5) is presumably protected from further reduction by dectrostatic factors. 

Figure 12 Oxidation of 2,4,6-trichlorophenol using the manganese complex of 5 and m-chloropcrbcnzoic acid...

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