Isocyclic Compounds
Full Access
ChemInform Abstract: Enol Ethers. Part 19. Investigations of the Autoxidation and the Rearrangement of (n)(2,4)Phloroglucinophanes.
First published: January 2, 1990
Abstract
Autoxidation of the (n)(2,4)phloroglucinophanes (I) gives the hydroperoxides (II) as the first oxidation products, which react to the more stable monohydroxylated compounds (III) with different rates.
ChemInform Abstract
Autoxidation of the (n)(2,4)phloroglucinophanes (I) gives the hydroperoxides (II) as the first oxidation products, which react to the more stable monohydroxylated compounds (III) with different rates. In alkaline solution (III) rearrange to cyclopentenones such as (IV). The acylphloroglucinophane (V), however, reacts with oxygen to give the dihydroxylated compound (VI). The phloroglucinophanes serve as model compounds for the oxidation of deoxyhumulone to humulone and its rearrangement into isohumulone, the bitter principle of hop.
