Configurational inversion and hexachloroethane chlorination of α-sulfonylcarbanions |
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| Authors: | J. Kattenberg E.R. De Waard H.O. Huisman |
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| Affiliation: | Laboratory of Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, Amsterdam, The Netherlands |
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| Abstract: | The cis fused bicyclic sulfones 1a, 1c and 3a are lithiated in benzene with n-butyllithium under concomitant cis/trans isomerization of the ring fusion, involving intramolecular proton transfer. H/D exchange of the three α-hydrogens in protic solvents proceeds with retention of configuration. The lithiated sulfones are chlorinated with hexachloroethane (HCE) and show a strong preference for introduction of halogen at an equatorial α-position. |
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| Keywords: | Address correspondence to this author. |
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