Perphthalic acid mono

Palmitic acid, 69 o-Pelargonylphenol, 58 P-Pelaigonylphenol, 58 Pentaacetyl d-CLUcononitrile, 14,74 2,4-PENTANEDIONE, 6 Pentose synthesis, 14 Perkin reaction, 55 Peroxide, removal, 95 Perphthalic acid, mono-, 70... 

Alkyl thietes may be oxidized in low yield to the sulfones with mono-perphthalic acid. An IR absorption at 1067cm suggested the presence of a sulfoxide in the oxidation of 228. Oxidation of the dialkyl thietes 229a and 229b with hydrogen peroxide in acetic anhydride gave 80-85% yields of ,J3-unsaturated aldehydes, possibly derived from an intermediate sulfoxide. The naphthothiete 205 yields either the sulfoxide or sulfone with w-chloroperbenzoic... 

Azetidinyl-4-ketones are closer than azetidinyl-4-carboxylic esters to the target 4-acyloxy derivatives 11, 29, 36. Thus, Hanessian s version of the threonine route [29], utilizing a-keto anions, can be considered an improvement over Shiozaki s a-carboxyanion strategy, especially when its aptitude for being scaled-up for industrial production is considered. The key-step, cyclization of amide 68a (prepared from epoxyacid 64 and fV-anisylphenacylamine) to azeti-dinone 28a, is carried out by simple treatment with K2CO3 at ambient temperature silylation, CAN-mediated cleavage and oxidation with mono-perphthalic acid complete the sequence to synthon 29b. 

This method was introduced by Polonski and Chimiak 192,193) in 1974 (Scheme 47). It is based on the oxidation of Schiff bases (239) to appropriate oxaziridines (240) in ether using monoperphtalic acid (MPP). Bases (239) are obtained from esters of amino acids and anisyl aldehyde (238) and are oxidised without isolation. Oxaziridines (240) are next hydrolyzed with hydrochloric acid to N-hydroxyamino acids (1) or give p-toluenesulfonates of (76, 213), which crystallize readily, by splitting with hydroxylamine j7-toluenesulfonates in alcohol. Use of benzaldehyde is unfavourable and leads to nitrones. Use of mono-perphthalic acid permits one to follow the progress of the reaction due to precipitation of phthalic acid. This method is general. Because bases (239) racemize only very slowly it is possible to obtain 193) optically active compounds (1,76, 213). 

Chien and Amin (1980) have reported the preparation of 5,6-epoxy-5,6-dihydroretinoic acid (LXIII) labeled with tritium in position 11. The compound was readily obtained from the tritiated retinoic acid by epoxidation with mono-perphthalic acid (Fig. 17). 

The preparation of peracetic, performic, perbenzoic, and mono-perphthalate acids have been described. m-Chloroperbenzoic acid is available it has the advantage of being more stable than perbenzoic acid. Higher aliphatic peracids have been prepared in sulfuric acid as a solvent with 50% hydrogen peroxide. 

The epoxidation of an alkene with peracid to give an oxirane. The commercial available mCPBA is a widely used reagent for this conversion, while magnesium mono-perphthalate and peracetic acid are also employed. 

Pre-formed peracids used in the laboratory include 3-chloroperbenzoic acid, which is long-established in synthesis [20], and magnesium mono-perphthalate, a more recent addition [21]. 

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