Perbenzoic acid, m-Chloro-

Perbenzoic acid, m-chloro- [Benzenecar-boperoxoic acid, 3-chloro-J, 55, 88 PHASE TRANSFER ALKYLATION, 55, 91 PHASE TRANSFER CATALYSIS, 55, 96 Phenol, thio- [Benzenethiol], 55, 122 Phenol, 2,4,6 tnbromo-, 55, 20 m-Phcnylenediamine [1,3 Benzenediamine], p-bromination of, 55, 23 Phosphine, phenyl-, bis(3-dimethylamino-... 

Pentanol, 52, 22 trans-2-Pentenal, 4-hydroxy-4-methyl-, 54, 27 Pent-l-en-3-ol, 52, 22 trans-3-PENTEN-2-ONE, 51, 115 PERBENZOIC ACID, m-CHLORO-,... 

Pentynoic acid, 5-hydroxy-, 56, 51 2-Pcntynoic acid, methyl ester 55, 76 Peptides, 56, 88 Peracetic acid, 55, 87, 88 Perbenzoic acid, m-chloro-, 55, 88 Perbenzoic acid, 3-chloro-, 56, 1 Peroxydisulfunc acid ([(HO)S-(0)2 ] 2 Ot), diammomum salt, 56, 69 PHASE TRANSFER ALKYLATION, 55,... 

Diastereoselective epoxidations.6 Epoxidation of the ergoline 1 with m-chloro-perbenzoic acid provides the a-epoxide (2) with high diastereoselectivity and yield. In contrast, epoxidation via the bromohydrin provides the (1-oxide (2) in equally high diastereoselectivity. Osmylation of 1 also provides the 5a,6a-diol selectively (7 1) with similar preference for the a-face. 

Chloro 6 nitro toluene bifenox, fomesafen, lactofen, perfluidone m-Chloro perbenzoic acid fipronil, rimsulfuron m-Chlorophenol cloprop, 3 CPA, oxyfluorfen... 

The order of reactivity of the peroxy acid increases with the pKa value, i.e. peroxytrifluoroacetic > monopermaleic > />-nitroperbenzoic > m-chloro-perbenzoic > performic > perbenzoic > peracetic. 

Oxaphosphiranes are interesting as they are analogs of the well-known oxiranes (epoxides). The direct epoxidation of free phosphaalkenes most likely would be complicated or thwarted by oxygen attack at phosphorus. An elegant route to oxaphosphirane complexes 10a,b makes use of the quantitative oxydation of Tj -phosphaalkene complexes 9a,b with m-chloro-perbenzoic acid in THF see Eq. (4).8... 

B. a,a -Dibromodibenzyl sulfone. To a gently refluxing solution of 11.35 g. (0.053 mole) of dibenzyl sulfide in 150 ml. of carbon tetrachloride (Note 2) contained in a three-necked round-bottomed flask there is added dropwise over a period of 1.5 hours a solution prepared from 17.6 g. (0.11 mole) of bromine dissolved in 50 ml. of carbon tetrachloride while a sunlamp (Note 3) is focused on the reaction mixture from a distance of 1 in. The solution is refluxed by means of a heating mantle for 3 hours and the carbon tetrachloride removed from a water bath at 50° with the aid of a water aspirator. To the residual dark oil there is added 25 ml. of anhydrous ether (Note 4), and after cooling in an ice bath a solution of 32.5 (0.15 mole) of m-chloro-perbenzoic acid (Note 5) in 150 ml. of anhydrous ether is added dropwise over a 30-minute period. The mixture is then allowed to warm to room temperature and stirred for 2 days. 

A -chlorotriazole, dinitrogen tetroxide, chromic acid, chromium trioxide/ A -arylsulfonyl oxaziridines, azaaromatic A -oxides, and aryldimethylamine oxides. Overoxidation to the sulfone, which is a complication with hydrogen peroxide and the peracids, may be minimized by use of only one equivalent of oxidant and low temperatures. Sodium metaperiodate, m-chloro-perbenzoic acid, and hydrogen peroxide in acetone are often the oxidants of choice when the convenient hydrogen peroxide-acetic acid method is unsatisfactory. When particularly mild conditions (CHCI3, 25°) are desired, the oxaziridines may be useful (no acids or bases are present). 

Thietanone 1,1-dioxides are unknown, although the tetraphenyl compound may be an intermediate in the oxidation of the 2-thietanone 308 with m-chloro-perbenzoic acid to the sulfinic-carboxylic acid anhydride 331. The methods discussed below apply to 3-thietanone 1,1-dioxides and derivatives. 

When the ethoxycarbonyl ylid 60 (R = C02Et) is treated with m-chloro-perbenzoic acid, the sulfoxilimine 64 (R = C02Et) is formed in high yield. 

DMAc N,N-dimethyl acetamide MCPBA m-chloro perbenzoic acid... 

The structure of bucharaine has now been confirmed by synthesis (Scheme 25). The geranyl ether 286 was prepared from 4-hydroxy-2-quinolone and geranyl chloride. Selective epoxidation with m-chloro-perbenzoic acid yielded monoepoxide 287. Reaction of the epoxide with formic acid gave the formate ester 288, which on treatment with base was converted into bucharaine (206). 

With (—)-tabersonine (28) as the starting material and m-chloro-perbenzoic acid as the oxidizing agent followed by reaction with tri-phenylphosphine in acid, the corresponding 14,15-dehydro compounds,... 

---