Selenoxide elimination chemistry

PhS-SPh will do similar chemistry however a sulfoxide elimination is less facile than a selenoxide elinimation. 

Recently, Wirth and Uehlin further extended the selenium-based solid-phase assisted chemistry by introducing a new polymer-bound chiral selenium electrophile 29. Regio-and stereoselective 1,2-methoxyselenylation of propenylbenzene gave intermediate adduct 30 which was cleaved by oxidative elimination via the selenoxide to yield the corresponding allylmethyl ether (Scheme 12) [38]. 

As already mentioned, the ry -elimination of selenoxides was discovered around 197010 and had a major impact on the development of organoselenium chemistry. This reaction is about three orders of magnitude more rapid than the elimination of the corresponding less polar and less basic sulfoxides. Sigmatropic rearrangements proceed at markedly lower temperatures. These reactions are discussed in detail in Section 9.11.2.5. 

Synthese of Alkylidene cyclopropanes Via the Selenoxide Route The synthesis of olefins by oxidative elimination of selenides is one of the most versatile and useful methods in selenium chemistry reaction usually... 

Vinylic ether-containing Claisen rearrangement substrates may be generated using syn-elimination reactions of sulfoxides, selenoxides, and selenones. 2-(Arylsulfinyl)ethyl ethers are particularly useful substrates in these reactions because of their ready availability by nucleophilic addition of allylic alcohols to commercially available phenylsulfinylethene. Scheme 13.27 shows a typical synthetic context for this chemistry, involving the stereospecific introduction of quaternary centers from easily accessed allylic alcohol precursors." ... 

Grieco, P. A. Gilman, S. Nishizawa, M. Organoselenium Chemistry. A Facile One-Step Synthesis of Alkyl Aryl Selenides from Alcohols /. Or. Chem. 1976, 41, 1485-1486. Sharpless, K. B. Young, M. W. Olefin Synthesis. Rate Enhancement of the Elimination of Alkyl Aryl Selenoxides by Electron-Withdrawing Substituents / Or . Chem. 1975, 40, 947-949. 

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