Novel episulfone substitution and ring-opening reactions via α-sulfonyl carbanion intermediates

Article abstract of DOI:10.1080/10426509708545519

Three-membered cyclic sulfones undergo substitution on treatment with base-electrophile mixtures, such as LDA-Me₃SiCl and ^tBu-P4-phosphazene base-PhCHO, to give either substituted episulfones or the corresponding alkenes following loss of SO₂-In the absence of Me₃SiCl, reaction of episulfones with LDA results in ring-opening to give alkenyl sulfinate intermediates, which can be alkylated to give (E)-alkenyl sulfone products in stereoselective fashion.

Full text of DOI:10.1080/10426509708545519

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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Novel Episulfone Substitution and
Ring-Opening Reactions via α-
Sulfonyl Carbanion Intermediates
Nigel S. Simpkins
a The Department of Chemistry , The University of
Nottingham , University Park, Nottingham NG7 2RD, U.K.
Published online: 17 Mar 2008.
To cite this article: Nigel S. Simpkins (1997) Novel Episulfone Substitution and Ring-
Opening Reactions via α-Sulfonyl Carbanion Intermediates, Phosphorus, Sulfur, and Silicon
and the Related Elements, 120:1, 197-211, DOI: 10.1080/10426509708545519
To link to this article: http://dx.doi.org/10.1080/10426509708545519
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