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Gem-Dimethyl-cyclo-propanation of dibenzyl-ideneacetone using triisopropyl sulfoxonium tetra-fluoro-borate
The reaction between dibenzyl-ideneacetone (dba) and tri-isopropyl sulfoxonium tetra-fluoro-borate has been reinvestigated. The stereochemistry of the major diasteromeric bis-(gem-dimethyl-cyclo-propane) adduct has now been assigned as [(1RS,3RS)-2,2-dimethyl-3-phenyl-cyclo-prop-yl][(1SR,3SR)-2,2- dimethyl-3-phenyl-cyclo-prop-yl]methanone, C23H26O, by X-ray crystallographic studies on a twinned crystal. The asymmetric unit contains two ml-ecules of the adduct, the conformations of which differ in the orientation of the phenyl ring relative to the adjacent cyclo-propanated double bond. The carbonyl groups of each adduct are aligned approximately along the a axis and in opposite directions to each other. The mol-ecules pack to give a sinusoidal pattern along the b axis. This is the first acyclic bis-(dimethyl-cyclo-prop-yl) ketone for which an X-ray crystal structure determination has been reported, and is also the first bis-cyclo-propanated dba analogue. The knowledge that the major diastereomer has the meso structure (and therefore the confirmation that the minor isomer is the racemate) will prove invaluable in future studies to utilize bis-(dimethyl-cyclo-prop-yl) ketones as reagents, in rearrangement processes, and as potential ligands and ligand precursors in organometallic chemistry.
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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate