Oxidation by Solids. III. Benzalanilines from N-Benzylanilines and Related Oxidations by Manganese Dioxide

The Oxidation of Organic Compounds by Active Manganese Dioxide

“…starting with malonic ester lactone, the sequence involves a reductive elimination, to give an allylic alcohol, followed by an oxidative cyc1ization (Mn0 2 ), to give a lactone. This is demonstrated in the conversion of the cyc10heptane lactone ester (55) into a.-methylene lactone (57) via intermediate 56, and in a similar svnthesis of the dl-alantolactone (60) via intermediates 58 and 59.123.124 Cor~y and co-workers 125 …”

“…instead of the imino hydrogen atom (N -H). 60 The formation of free radicals 57 . 60 and hydroxylamines 49 • 57 as intermediate products in the oxidation of amines with manganese dioxide was suggested in early studies.…”

“…563 although corresponding azo compounds were obtained from 0-and p-nitroanilines. 60 The authors 563 found that para-substituted anilines react somewhat faster than other isomers; in general. electron-donating substituents on the ring (e.g., halogen or methoxy groups) favor the oxidation.…”

Strategien zur Erforschung neuer Reaktionen

“…[33] Beispiele sind hypervalente Iod-Reagentien, [34] Phenylselensäureanhydrid, [35] Mangandioxid [36] unter andere mehr. [37] Oxidationen von Aminen wurden auch mit katalytischen Menge von Ruthenium-Katalysatoren, [34c, 38] eines Cobalt-Schiff-Base-Komplexes [39] oder NiSO 4 [40] in Gegenwart eines Cooxidationsmittels durchgeführt.…”

Oxidation of Organic Compounds with Nickel Peroxide

“…Thus. the treatment of 44 with nickel peroxide in benzene at room temperature gives a mixture of several products consisting of [45][46][47][48][49][50][51] (Scheme (0). 34 4-Cyanocatechol (51) is oxidized by nickel peroxide to give an o-quinone intermediate which has been trapped with 2,3-dimethylbutadiene (53) to give the adduct 54 (Scheme ll).…”