On the Oxidation of 2-Hydroxy-1,4-naphthoquinone Derivatives with Alkaline Potassium Permanganate. Part II. Compounds with Unsaturated Side Chains^1,2

Light effect on the stability of β-lapachone in solution: pathways and kinetics of degradation

“…Similar compounds have been proposed to explain the Hooker's oxidation mechanism for 1,4-naphthoquinones. [24][25][26] 6-Hydroxy-3methylene-3H-isobenzofuran-1-one: Isolated degradation products were dissolved in distilled water and qualitatively analysed by HPLC using the same conditions as previously described. Chromatograms of compounds 2, 3, 4, 5 and 6 presented main peaks at shorter retention times (0.9-3.8 min) than bLAP (4.9 min) suggesting that the degradation products did not interfere on bLAP resolution using the selected HPLC method.…”

Metalloporphyrin-Catalyzed Oxidation of 2-Cycloalkyl-3-hydroxynaphthoquinones

“…The chemical oxidation of a series of 2-alkyl-3-hydroxynaphtho-1,4-quinones, again in particular 2-(3-methylbut-2-enyl)-3-hydroxynaphtho-1,4-quinone lapacol ( 1 , R = 3-methylbut-2-enyl, R‘ = H), was investigated by Hooker and reported in 1936 . He used a rather vigorous oxidant, alkaline KMnO 4 , and found a product in which the 2-alkyl group is shortened by one carbon (see Scheme ).…”

Lawsone in organic synthesis

“…185,188 This reaction has been used for the synthesis of a number of new naphthoquinones. [189][190][191][192] Fieser wrote the following in his memoir published in 1964: "A second reaction which proved to be extremely useful is a remarkable one discovered by Dr Hooker in retirement and known as the Hooker oxidation. On reaction of M-1926 (R ¼ (CH 2 ) 9 CH 3 in Scheme 23) with alkaline potassium permanganate in the cold, a CH 2 unit mysteriously disappear from the side chain".…”