154911-48-5Relevant articles and documents
SYNTHESES DE CYCLOHEXENONES α-SUBSTITUEES VIA LA THERMOLYSE DE CETOSULFOXYDES TERTIAIRES
Barillier, Daniel,Benhida, Rachid,Vazeux, Michel
, p. 83 - 96 (2007/10/02)
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-methylthiocyclohexanone 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 the resulting sulfoxides 2 have been performed.The scope and limitations of this strategy are also discussed. Key Words: α-functionalized cyclohexenones; tertiary ketosulfides and ketosulfoxides; sulfenylation and deshydrosulfenylation; thermolysis.