Coulometric generation of acetylions by oxidation of mercury in acetic anhydride and in acetic acid/acetic anhydride mixture

Coulometric generation of acetyl (CH₃CO⁺) ions by oxidation of mercury in acetic anhydride and in acetic acid/acetic anhydride (5:95, v/v) is described. Current/potential curves for solvents, titrated bases, indicator and mercury showed that in both these solvents mercury is oxidized at potentials which are much more negative than those for the titrated bases and other components present in the solution. Quinoline, triethanolamine, triethylamine, pyridine and quinolin-8-ol in acetic anhydride, as well as triethylamine, 2,2′-bipyridine, 2,4,6-collidine, pyridine and sodium acetate in acetic acid/acetic anhydride were titrated with acetyl ions generated by the oxidation of mercury. In this way, it was established that the oxidation of mercury to mercury (I) ions proceeds quantitatively with 100% current efficiency.     

The rearrangement polymerization of phosphorous acid with acetic anhydride

Phosphorous acid reacts with acetic anhydride to give almost quantitative yields of poly(ethane,1-hydroxy,1,1-diphosphonates); hydrolysis studies suggest the presence of the interlinked units

in the product.     

New possibilities in nitration with a mixture of nitric acid and acetic anhydride

Summary A mixture of nitric acid and acetic anhydride with a nitric acid content of 80 moles per cent has a considerably more powerful nitrating action than a mixture with 35–50 moles per cent of nitric acid. It is desirable to use this mixture for the nitration of furans with low sensitivity to electrophilic attack.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 103–110, January, 1965     

Conversions of allyl aryl sulfoxides under pummerer rearrangement conditions

In the presence of acetic acid, allyl phenyl sulfoxide forms -acetoxyallyl phenyl sulfide and 2-acetoxymethyl-2,3-dihydrobenzothiophene; under the same conditions allyl 1-naphthyl sulfoxide gives 2-methyl-2,3-dihydronaphtho-[1,2-b] thiophenoxide.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 747–749, June, 1985.     

Bromination of isoprene in acetic anhydride

Conclusions The reaction of bromine with isoprene in acetic anhydride as the medium proceeds as competing brominnation and bromoacetoxylation.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1675–1677, July, 1977.     

A straightforward approach to 2-azetidinones from imines and carboxylic acids using dimethyl sulfoxide and acetic anhydride

The direct synthesis of 2-azetidinones from imines and carboxylic acids under mild conditions is developed. Dimethyl sulfoxide (DMSO) can be activated by acetic anhydride and the resulting active species is used for the in situ generation of ketenes from carboxylic acids. This method is cheap, simple, convenient, and efficient and the products are easily isolated.     

Reaction of hexafluoroacetone with acetic anhydride

Conclusions When acetic anhydride reacts with hexafluoroacetone it acts not as an acetylating agent, but as a compound containing an active methylene group.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 1661–1662, September, 1966.     

Multiphase telomerisation of butadiene with acetic acid and acetic anhydride

Two different routes to acetoxyoctadiene are presented. The first one uses the well-known telomerisation of butadiene with acetic acid operating in a multiphase semi-batch mode. The second reaction involves the cleavage of acetic anhydride, hydrogen transfer via ketene formation and thus a telomerisation as well.     

Cyclization of 4-ureidobutanoic acids in acetic anhydride

A simple method is proposed for synthesizing 1-carbamoyl-2-pyrrolidones by cyclization of 4-ureidobutanoic acids in acetic anhydride.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 33–38, January, 1995.     

Oxidation of p-cresol with ozone in acetic anhydride

Preparation of aromatic alcohols and aldehydes by oxidation of p-cresol with ozone in acetic anhydride in the presence of sulfuric acid, manganese acetate, and potassium bromide was studied. The optimal oxidation conditions were determined.     

Oxidation of 4-hydroxytoluene with an ozone-oxygen mixture in acetic acid

Liquid-phase oxidation of 4-hydroxytoluene by ozone to 4-hydroxybenzoic acid in the presence of cobalt(II) acetate as a catalyst was studied. The optimal oxidation conditions were found.     

The action of acetic anhydride on N-methyltryptophans

Summary A new furocoumarin of composition C₂₁H₂₂O₇ has been isolated from the fruit ofLibanotis transcaucasica Schischk. It has been established that libanotin is a derivative of 8-isopropyloxy-8,9-dihydroangelicin. The side groups of libanotin — acetic and 2-methyl-cis-crotonic acids — are attached to the main part of the molecule by ester bonds.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 3, pp. 215–220, 1965