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Literature DB >> 20704444

Silylene transfer to allylic sulfides: formation of substituted silacyclobutanes.

Bryan J Ager¹, Laura E Bourque, Kay M Buchner, K A Woerpel.

Abstract

Silylene transfer to allylic sulfides results in a formal 1,2-sulfide migration. The rearrangement yields substituted silacyclobutanes, not the expected silacyclopropanes. The silacyclobutanes were elaborated by insertions of carbonyl compounds selectively into one carbon-silicon bond. A mechanism for the 1,2-sulfide migration is proposed involving an episulfonium ion intermediate.

Entities: Chemical Gene

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Year: 2010 PMID： 20704444 PMCID： PMC4037888 DOI： 10.1021/jo1008228

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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References

15 in total

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Authors: Koji Hirano; Hideki Yorimitsu; Koichiro Oshima
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Authors: Koji Hirano; Hideki Yorimitsu; Koichiro Oshima
Journal: Org Lett Date: 2008-05-06 Impact factor: 6.005

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10. Formation and utility of oxasilacyclopentenes derived from functionalized alkynes.

Authors: Timothy B Clark; K A Woerpel
Journal: J Am Chem Soc Date: 2004-08-11 Impact factor: 15.419

Silylene transfer to allylic sulfides: formation of substituted silacyclobutanes.

1. Nickel-catalyzed reactions of silacyclobutanes with aldehydes: ring opening and ring expansion reaction.

2. Metal-catalyzed silylene insertions of allylic ethers: stereoselective formation of chiral allylic silanes.

3. Synthesis of allylsilanes by reductive lithiation of thioethers.

4. Palladium-catalyzed formal cycloaddition of silacyclobutanes with enones: synthesis of eight-membered cyclic silyl enolates.

5. Au-catalyzed reaction of propargylic sulfides and dithioacetals.

6. Mechanism of di-tert-butylsilylene transfer from a silacyclopropane to an alkene.

7. Metal-catalyzed di-tert-butylsilylene transfer: synthesis and reactivity of silacyclopropanes.

8. Mechanism of silver-mediated di-tert-butylsilylene transfer from a silacyclopropane to an alkene.

9. On the mechanism of arene-catalyzed lithiation: the role of arene dianions--naphthalene radical anion versus naphthalene dianion.

10. Formation and utility of oxasilacyclopentenes derived from functionalized alkynes.