Tetrahedron p. 5045 - 5050 (1985)
Update date:2022-07-30
Topics: Yield Catalyst reflux Neutralization Filtration GC (gas chromatography) Stereoisomers Reaction Mechanism Solvent and Temperature Catalyst and Ligand Selection Chelation Control
Hatzigrigoriou, E.
Wartski, L.
Seyden-Penne, J.
Toromanoff, E.
Conjugate addition of carbanionic reagents formed from aryl- or phenyl-thioacetonitriles 1a-c and 2 to 2-methyl and 2-phenyl 2-cyclohexenone or 2-methyl 2-cyclopentenone, followed by acidic quench, under kinetic control, leads to different ratios of cis and trans 2,3-disubstituted cyclanones according to ring size.From 2-methyl and 2-phenyl 2-cyclohexenone, the cis isomer is highly predominant (85 to 98percent).From 2-methyl 2-cyclopentanone a cis/trans mixture is obtained: the cis isomer only predominates when a bulky reagent (1c) is used (80percent); in the other cases a mixture of nearly 1:1 is obtained.
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