- Gas-Phase Reactions of 1,2-Dimethylcyclopentene and of 2,6-Heptanedione with Ozone: Unprecedented Formation of an Ozonide by Ozone Treatment of a Diketone
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Gas-phase ozonizations of 1,2-dimethylcyclopentene (1) and of 2,6-heptanedione (5) afforded in each case dimethylcyclopentene ozonide (2) in low yields. In the ozonization of 1, diketone 5 was formed as the single major product, along with nine "abnormal" ozonolysis products which were formed by oxidative cleavage of carbon-carbon single bonds.
- Griesbaum, Karl,Miclaus, Vasile,Jung, Chan,Quinkert, Ralf-Olaf
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- Regioselective synthesis of α,α-dialkylcyclopentanones from 1-hydroxycyclobutanecarboxylic acid or from O-protected cyclobutanone cyanohydrin
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1-(1-Hydroxyalkyl)cyclobutanols 4a-f, readily available either from 1-hydroxycyclobutane carboxylic acid or from O-protected cyclobutanone cyanohydrin, appeared the most suitable precursors for a regioselective synthesis of cyclopentanones α,α- disubstituted with various similar or different alkyl, alkenyl, aryl or cycloalkyl groups. The key steps consist of acid or Grignard reagent induced C4→C5 ring expansions.
- Estieu, Karine,Ollivier, Jean,Salauen, Jacques
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p. 8075 - 8090
(2007/10/03)
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