Monoperoxyphthalate

Three peroxyacids are produced commercially for the merchant market peroxyacetic acid as a 40 wt % solution in acetic acid, y -chloroperoxybenzoic acid, and magnesium monoperoxyphthalate hexahydrate. Other peroxyacids are produced for captive use, eg, peroxyformic acid generated in situ as an epoxidizing agent. 

JV-Oxidation of phthalazine with monoperoxyphthalic acid produces the corresponding... 

MMPP-6H20 (magnesium monoperoxyphthalate), pH 7 buffer, MeOH, 0°, 5-120 min, 76-99% yield. These conditions were used to cleave the related SAMP hydrazone in the presence of two trisubstitued alkenes in 46% yield. ... 

Many other reagents for converting alkenes to epoxides,including H2O2 and Oxone , VO(0-isopropyl)3 in liquid C02, ° polymer-supported cobalt (II) acetate and 02, ° and dimethyl dioxirane.This reagent is rather versatile, and converts methylene oxiranes to spiro-epoxides. ° ° One problem with dimethyloxirane is C—H insertion reactions rather than epoxidation. Magnesium monoperoxyphthalate is commercially available, and has been shown to be a good substitute for m-chloroperoxybenzoic acid in a number of reactions. 

It is possible to oxidize dimethylhydrazones R—C=N—NMe2 to the corresponding nitrile (R—C=N) with MeRe03/H202 magnesium monoperoxyphthalate... 

C(,H7N06 1955-46-0) see lotalamic acid loxitalamic acid monomethyl 2-(2-thienylmethyl)malonate (C9H10O4S 122308-24-1) see Eprosartan monoperoxyphthalic acid... 

MMPP = monoperoxyphthalate hexahydrate D Annibale, A. Scettri. A. Tetrahedron Lett, 1995, 36, 4659... 

Pyrazolo[l,2-r-][l,3,4]oxadiazine derivative 188 is converted to the corresponding (V-oxide 189 by oxidation with magnesium monoperoxyphthalate (MMPP) or -chloroperbenzoic acid (MCPBA) (Equation 23) <2004CEJ737>. 

Dg]-butadiene monoepoxide, 8, has been synthesized2 by treating the water solution (pH 5.5) of magnesium monoperoxyphthalate hexahydrate at room temperature with [Dg]-1,3-butadiene at 1 atmosphere in 94% yield after 50 min reaction time. Under these conditions less than 1% of butadiene diepoxide has been formed as determined by GC/MS. The concentration of the [Dg]-butadiene monoepoxide in the aqueous reaction mixture at various reaction times has been determined by selective ion monitoring of ions with mjz... 

Alternatively, Ballini devised a new strategy to synthesize tri-alkylated pyrroles from 2,5-dialkylfurans and nitroalkanes <00SL391>. This method involves initial oxidation of 2,5-dimethylfuran with magnesium monoperoxyphthalate to cA-3-hexen-2,5-dione (6). Conjugate addition of the nitronate anion derived from the nitro compound 7 to 6 followed by chemoselective hydrogenation of the C-C double bond of the resulting enones 8 (obtained by elimination of nitrous acid from the Michael adduct) completes the conversion to the alkylated y-diketones 9. Final cyclization to pyrroles 10 featured improved Paal-Knorr reaction conditions involving reaction of the diketones with primary amines in a bed of basic alumina in the absence of solvent. 

The synthesis of oxaziridine-fused quinazolinones 277 follows a different route. Quinazolinones 274 (R = Et, nPr, n-hexyl) can readily be prepared by reacting 2-oxo-l-cyclohexanecarboxamide with aldehydes in the presence of ammonia solution. In the reaction of 274 and monoperoxyphthalic acid, the hydroxyoxaziridines 277 were formed via the presumed intermediates 275 and 276. No spectroscopic evidence was given for 277, nor was its relative configuration investigated [76JPR(318)895]. 

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