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Photochemistry of β-hydroxy-γ-pyrone. A new synthesis of 3-methylcyclopent-2-en-2-ol-1-one from maltol

✍ Scribed by Masao Shiozaki; Tetsuo Hiraoka


Publisher
Elsevier Science
Year
1972
Tongue
French
Weight
166 KB
Volume
13
Category
Article
ISSN
0040-4039

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✦ Synopsis


While photorearrangements of cross-conjugated cyclic dienones are well knownl, the photochemistry of If-pyrone is limited in its utility since a complex rearrangement was encountered in addition to dime-.zation. 2 This complexity depends upon the nature of an intermediate zwitterion, whose intermolecular nucleophilic trapping was achieved in the cyclohexadienone system by Schuster et al. 3 This evidence suggests that intramolecular quenching of the zwitterion generated from p-pyrone by photochemistry would give a clear-cut product. Thus a hydroxyl group situated at the S-position in a r-pyrone derivative would be


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