Silver permanganate, preparation

TL5981>. The proposed mechanism involves the oxidation of the amine to an imine, tautomerization to an enamine, and a sequence of nucleophilic attacks on the pyridazine rings followed by oxidation steps. The oxidant of choice is (bispyridine)silver permanganate <1982TL1847>, which is easily prepared, mild in action, and is soluble in organic media. If R1 = H in the product 77, electrophilic substitution (e.g., bromination, nitration, Mannich, and Vilsmeier-Haack-Arnold reactions) occurs at this position. 

Silver permanganate [7783-98-4] M 226.8, df 4.49. The salt forms violet crystals which can be crystallised from hot H2O (soluble is 9g/L at 20°). Store it in the dark. This oxidising agent is decomposed by light. [Lux in Handbook of Preparative Inorganic Chemistry (Ed. Brauer) Academic Press Vol I p 1463 1963.]... 

Thiele prepared aliphatic compounds of tervalent iodine and aliphatic iodoso-, iodo-, and iodonium compounds, and aliphatic azo-compounds. In World War I he introduced respirators containing silver permanganate as protection against carbon monoxide formed by the explosion of grenades in confined spaces. 

Pinoglycyl Acetate.—This ester can be prepared by the direct acetylation of pinoglycol, C,gH,.0(0H)g, an alcohol resulting from the oxida-.tion of pinol with permanganate of potassium. It can also be prepared from pinol dibromide and acetate of silver. It is an ester with an excellent fruity odour, of the formula C,gH, 0(CgHg0.2).2, melting at 97° to 98°, and boiling at 155° at 20 mm. pressure, or at 127° at 13 mm. 

Diols are prepared from alkenes by oxidation with reagents such as osmium tetroxide, potassium permanganate, or hydrogen peroxide (Section 11-7C). However, ethylene glycol is made on a commercial scale from oxacy-clopropane, which in turn is made by air oxidation of ethene at high temperatures over a silver oxide catalyst (Section 11-7D). 

The most widely used routes to benzo[ >]thiophene-2-carboxylic acids are (a) successive lithiation and carbonation of the parent benzo[ >]thiophene,42,76 90 98,183,477, 481>487,521,685-687 (ft) oxidation of the corresponding aldehyde,90,91,106,189 424, 477,640 (c) hypohalite oxidation of the corresponding methyl ketone,82 °8,189,424 and (d) cyclization reactions (Section IV,D, and E). Acids prepared by these routes are listed in Table XV. Oxidation of aldehydes usually proceeds almost quantitatively with moist silver oxide,90,91,105, 189,424 hut potassium permanganate is satisfactory.477, 640... 

Allyl olefines are mainly used and, from these reactants, Brace prepared diols and diacids by reacting silver acetate and by permanganic oxidation, respectively [65]. 

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