70989-98-9Relevant articles and documents
Chemistry of free cyclic vicinal tricarbonyl compounds ('1,2,3-triones'). Part 2. Redox reactions of 1,2,3-triones with ene-1,2-diols ('reductones'), 2-alkoxy-en-1-ols, ene-1,2-diamines, and related species
Schank, Kurt,Bouillon, Guenter,Fuenfrocken, Michael,Lick, Carlo,Lieder, Robert
, p. 1295 - 1326 (2007/10/03)
Midstanding carbonyl groups of cyclic 1,2,3-triones 4 possess outstanding electrophilic (electron-pair accepting) as well as oxidizing (one-electron accepting) properties. Their reactions with selected electron-rich C=C bonds as efficient nucleophiles AN reactions) and as efficient reducing agents (SET (single electron transfer) reactions) are studied. In a few cases, short-lived charge-transfer colors be observed. Particularly, free didehydro-5,6-O-isopropyliden-L-ascorbic acid (4g), its O,C-adduct 8g to 5,6-O-isopropylidene-L-ascorbic acid (1g), and via an independent pathway - the ostensible C,C-dimer 10a of mono-dehydrodimedone reductone were prepared. Intermediate radical anions 4 can be considered to be ideal representatives of dicapto-dative radicals. Novel large-scale syntheses of 3,4-dihydroxyfuran-2(5H)-one (1e) and of its vicinal trione 4e are presented.
