SYNTHESES DE CYCLOHEXENONES α-SUBSTITUEES VIA LA THERMOLYSE DE CETOSULFOXYDES TERTIAIRES

D Barillier, R Benhida, M Vazeux

Index: Barillier, Daniel; Benhida, Rachid; Vazeux, Michel Phosphorus, Sulfur and Silicon and the Related Elements, 1993 , vol. 78, # 1-4 p. 83 - 96

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Citation Number: 3

Abstract

Abstract The sulfenylation-dehydrosulfenylation method, combined with carbon-carbon bond forming reactions, has been applied to the synthesis of some α-functionalized cyclohexenones 3. Hence, the sodium anion of the 2-méthylthiocyclohexanone in THF reacts with primary, allyl and benzyl halides as well as with Michael acceptors to lead to the tertiary ketosulfides 1a-j. Further oxidation by NaIO4 and thermolysis in boiling toluene of ...