Scope and limitations in the use of α-silyl and α-stannyl sulfones as latent α-sulfonyl anions

Article abstract of DOI:10.1080/00397919108021069

Three methods for the regeneration of α-sulfonyl anions from α-silyl sulfones and α-stannyl sulfones are investigated. These methods include: (1) treatment of α-silyl sulfones with electrophiles (aldehydes and acid halides) in the presence of fluoride ion; (2) reaction of α-silyl sulfones with n-butyllithium which produces an α-silyl anion via a migration of the -SiMe₃ group from the α-position to the ortho-position of the phenyl sulfones; and (3) direct transmetalation of α-stannyl sulfone by treatment with n-butyllithium. The addition of cerium [III] chloride is shown to substantially decrease enolization problems associated with addition of α-sulfonyl anions to carbonyl compounds bearing enolizable protons.

Full text of DOI:10.1080/00397919108021069

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Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
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Scope and Limitations in the
Use of α-Silyl and α-Stannyl
Sulfones as Latent α-Sulfonyl
Anions
M. Lamothe a , M. B. Anderson a & P. L. Fuchs a
a Department of Chemistry , Purdue University ,
West Lafayette, Indiana, 47907
Published online: 23 Sep 2006.
To cite this article: M. Lamothe , M. B. Anderson & P. L. Fuchs (1991) Scope and
Limitations in the Use of α-Silyl and α-Stannyl Sulfones as Latent α-Sulfonyl Anions,
Synthetic Communications: An International Journal for Rapid Communication of
Synthetic Organic Chemistry, 21:15-16, 1675-1693, DOI: 10.1080/00397919108021069
To link to this article: http://dx.doi.org/10.1080/00397919108021069
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