Synthesis of 2-arylcycloalka-2,4-dienones using sulfone-based methodology.
Addition of the anion derived from (phenylthiomethyl)phenyl sulfone to a selection of aryl omega-alkenyl ketones gives adducts that via a sequence of Lewis acid catalyzed rearrangement, alpha-allylation, and metathesis give rise to 2-thio-4-cycloalkenones. These in turn give cycloalkadienones upon oxidation and elimination. An attempt to develop a polymer-supported variant fails because of the reversibility of sulfone anion addition.
Department of Chemistry, University of California, Davis, California 95616, USA.
Saphon
S
Hok
Neil E
NE
Schore