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Chemie freier cyclischer vicinaler Tricarbonyl‐Verbindungen (‘1,2,3‐Trione') Teil 2. Redox‐Reaktionen von 1,2,3‐Trionen mit En‐1,2‐diolen (‘Reduktonen'), 2‐Alkoxy‐en‐1‐olen, En‐1,2‐diaminen und verwandten Spezies
Author(s) -
Schank Kurt,
Bouillon Günter,
Fünfrocken Michael,
Lick Carlo,
Lieder Robert
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200205)85:5<1295::aid-hlca1295>3.0.co;2-k
Subject(s) - chemistry , electrophile , oxidizing agent , vicinal , nucleophile , medicinal chemistry , ascorbic acid , adduct , redox , organic chemistry , catalysis , food science
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 . 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 CC bonds as efficient nucleophiles ( A N reactions) and as efficient reducing agents (SET (single electron transfer) reactions) are studied. In a few cases, short‐lived charge‐transfer colors could 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(5 H )‐one ( 1e ) and of its vicinal trione 4e are presented.