- EINFACHE, REGIOSPECIFISCHE SYNTHESE VON CYCLOALKENONEN AUS LACTONEN
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The reaction of lithiumalkylphosphonates with γ- or δ-lactones followed by oxidation leads to 2,5- or 2,6-dioxophosphonates, which can be cyclized to cyclopentanones or cyclohexanones, respectively, constituting an easy, regiospecific route to cycloalkanones from lactones.
- Altenbach, Hans-Josef,Holzapfel, Winfried,Smerat, Gerd,Finkler, Stefan H.
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p. 6329 - 6332
(2007/10/02)
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- Strategic Synthesis based on Cyclohexadienes: Preparation of 2-, 2,3- and 2,4-Substituted Cyclohexenones; Synthesis of (Z)-Heneicosa-6-en-11-one
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The mesomeric anions, generated from 1-methoxycyclohexa-1,4-diene, 1-methoxy-5-methylcyclohexa-1,4-diene, and 1-methoxy-4-methylcyclohexa-1,4-diene with potassium amide in liquid ammonia, have been readily alkylated and the resulting dienes were hydrolysed to yield 2-alkyl-, 2,3-dialkyl- and 2,4-dialkyl-cyclohex-2-enones in good yield.Arylation of the above mesomeric anions followed by hydrolysis afforded 2-arylcyclohex-2-enones in addition to substituted biphenyls.A new and efficient synthesis of the male sex attractant of the Douglas Fir Tussock Moth, (Z)-heneicosa-6-en-11-one is described using the above methodology.
- Pramod, Kakumanu,Ramanathan, Halasya,Rao, G. S. R. Subba
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- CYCLIC VINYL ETHER CARBANIONS-II PREPARATION AND APPLICATIONS TO THE SYNTHESIS OF CARBONYL COMPOUNDS
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Conditions for metalation of a variety of cyclic vinyl ethers and reaction of the resulting carbanions with electrophiles are described.Effects of the vinyl ether structure on the relative rates of metalation are discussed.Applications of this methodology
- Boeckman, Robert K.,Bruza, Kenneth J.
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p. 3997 - 4006
(2007/10/02)
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