Electrophilic Ene-type Reactions of Phenyl Vinyl Sulfoxide With Alkenes
(1993) Royal Society of Chemistry. Journal: Perkin Transactions 1 — n° 19, p. 2275-2280 (1993)
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- Abstract
- Phenyl vinyl sulfoxide 1 can be made to react as an alpha,beta-dicarbocation with alkenes by formation of one or two new C-C bonds. These reactions take place at or below room temperature, under the conditions of the Pummerer reaction, i.e. trifluoroacetic acid and its anhydride. The key step is an electrophilic ene-type reaction between a thionium ion and the alkene. The primary beta-trifluoroacetoxy sulfides thus formed then undergo rearrangement via an episulfonium ion to the more stable, secondary isomer.
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Harvey, J., Brichard, MH., & Viehe, HG. (1993). Electrophilic Ene-type Reactions of Phenyl Vinyl Sulfoxide With Alkenes. Royal Society of Chemistry. Journal: Perkin Transactions 1, 19, 2275-2280. https://doi.org/10.1039/p19930002275 (Original work published 1993)