Etude des petits cycles—XXXVI. Photo-oxygenation d'alkylidenecyclopropanes. Syntheses specifiques d'alkenylcyclopropanols,de β′-hydroxy α-enones et d'α,α′-dienones |
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Authors: | G Rousseau P le Perchec JM Conia |
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Abstract: | The dye-sensitized photo-oxygenation of alkylidenecyclopropanes 1a–4a at –50°C gives the hydroperoxydes 1b–4b, which were reduced in situ by PPh3 into 1-alkenylcyclopropanols 1c–4c in high yield. At higher temperatures, 1b–4b rearranged exclusively into β′-hydroxy α-enones 1d–4d if pyridine was added (α,α′-dienones 1e–4e are also formed competitively in absence of pyridine). At 3°C the photosensitised oxygenation of alkylidenecyclopropanes 1a–4a gives ketones 1k–4k, cyclobutanones 1i–4i and β′-hydroxy α-enones 1d–4d. The origin of products is discussed. |
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