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Extra resources for The Retinoids

Example text

Investigations of the mechanism of protonation of anhydroretinol (58) with anhydrous hydrogen chloride showed that very complex ionic mixtures were formed (Bulgrin and Lockhart, 1974). The retinyl carbonium ion (λ = 585 nm) has been characterized in the protonation of retinol (1) (Bobrowski and Das, 1982). The color change after protonation with about 80% sulfuric acid was utilized for the quantitative determination of retinoic acid (3). The acids (51) and (52), after quenching of the red carbonium ions, were determined to be rearrangement products (Tsukida et aL, 1978a, 1980, 1981; Ito etaL, 1980).

The direct oxidation of methyl retinoate (43) with manganese(IV) oxide to give methyl 4-oxoretinoate (317) has been described (Rao etaL, 1972; Henbest, 1957; Barua and Ghosh, 1972; Sokolova et aL, 1980). In this manner, retinoids 58 Fritz Frickel in which the allylic ring position is substituted by oxygen functional groups were obtained directly from commercial substances. However, the problem of this method is the apparent difficulty of obtaining manganese(IV) oxide with a welldefined oxidative ability.

82) Under more drastic reaction conditions, it was found that the cyclohexene ring of (24) underwent oxidative cleavage to give the diketo acid ester (236) (Schwieter etaL, 1971). In (4 + 2) cycloaddition reactions, retinoids act as diene components. Maleic anhydride underwent rapid addition at the terminal double bonds of (all-£)retinol (1) to give the 1:1 adduct (83) (Robeson et aL, 1955b). (83) The reaction proceeded very much more slowly when one of the two double bonds Δ > or Δ * had the cis configuration.

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