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The “Tocopherol−Acetaminophen Reaction” − A New [1,4]-Rearrangement Discovered in Vitamin E Chemistry

✍ Scribed by Thomas Rosenau; Paul Kosma

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 356 KB
Volume: 2001
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200103)2001:5<947::aid-ejoc947>3.0.co;2-r

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✦ Synopsis

Treatment of N-{4- [3,4-dihydro-6-hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-5-ylmethoxy]-phenyl}acetamide (8a)the Toc prodrug of acetaminophen (7)with aqueous base yields 4-hydroxy-3-(6-O-α-tocopheryl)acetanilide (10a) as the main product. This hitherto unknown reaction type can formally be regarded either as a rearrangement involving [1,4]-sigmatropic and [1,3]sigmatropic shifts, or as an intramolecular redox process. Alternative pathways, such as an intermolecular reaction or a free radical process, have been ruled out. The formation of 10a by a multi-step sequence consisting of elimination, redox reaction, 1,4-addition to a quinone intermediate, and re- [ ‡] Novel Tocopherol Derivatives, XII.

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