Vinyl Selenoxides Research Articles

ChemInform Abstract: Domino Michael-Seleno Pummerer Type Reaction (Additive Seleno Pummerer Reaction).

Domino Michael–seleno Pummerer type reaction (additive seleno Pummerer type rearrangement) has been realised by the reaction of 1,3-dicarbonyl compounds with vinyl selenoxides in the presence of amine and chlorosilane.

Domino Michael–seleno Pummerer type reaction (additive seleno Pummerer reaction)

Domino Michael–seleno Pummerer type reaction (additive seleno Pummerer type rearrangement) has been realised by the reaction of 1,3-dicarbonyl compounds with vinyl selenoxides in the presence of amine and chlorosilane.

ChemInform Abstract: Reactions of Vinyl Selenoxides and Ketenes via 3,3‐Sigmatropic Rearrangement.

AbstractThe vinyl selenoxides (I) react with dichloroketene (IIa) or chlorocyanoketene (IIb), generated by thermolysis of the azide (IV), yielding the phenylselenenyl γ‐lactones (III) or (V).

ChemInform Abstract: Competition Between Vinylic Substitution and Conjugate Addition in the Reactions of Vinyl Selenoxides and Vinyl Selenones with Nucleophiles in DMF.

AbstractThe starting vinyl selenoxides (I) and (IV) and vinyl selenones (IX) and (X) are obtained by MCPBA oxidation of the corresponding selenides in 42‐91% yield.

Reactions of vinyl selenoxides and ketenes via 3,3-sigmatropic rearrangement

The reactions of several vinyl selenoxides with chlorocyano-ketene proceed via a 3,3-sigmatropic rearrangement of an enolate oxyselenonium species to yield seleno-substituted γ-butyrolactones.

Competition between vinylic substitution and conjugate addition in the reactions of vinyl selenoxides and vinyl selenones with nucleophiles in DMF

Vinyl selenoxides and vinyl selenones present a different reactivity towards thiolate or alkoxide anions in DMF. In the case of selenoxides the addition of the nucleophiles regioselectively occurs at the α-carbon leading to the formation of the vinylic substitution products with complete retention of configuration. These reactions occur under very mild conditions indicating that the seleninyl group markedly enhances nucleophilic vinylic substitution rates. The results obtained with vinyl selenones are consistent with competitive nucleophilic attack at the α- and at the β-carbon. The former yields irreversibly the vinylic substitution products, whereas attack at the β-carbon leads to the reversible formation of selenonyl stabilized carbanions. The fate of these intermediates depends upon the nucleophilic reagent employed. With thiolate anions the vinyl selenones are rapidly subtracted from the equilibrium and the carbanion does not give any other product. With methoxide anions, on the contrary, the vinylic substitution is a slow process and the carbanion can give rise to conjugate addition products also. Malonate anions react only at the β-carbon of vinyl selenones and the resulting carbanions suffer proton transfer and intramolecular displacement of the selenonyl group to afford cyclopropane derivatives.

ChemInform Abstract: REACTIONS OF ENOLATES WITH VINYL SELENOXIDES AND VINYL SELENONES. ONE‐STEP SYNTHESIS OF CYCLOPROPYLCARBONYL COMPOUNDS

AbstractDie aus Carbonylverbindungen (I) gebildeten Enolatanionen reagieren mit entsprechenden Vinylselenoxiden (II) (durch einen prim. konjugierten Additions‐ und nachfolgenden Substitutionsprozeß; Diskussion des Mechanismus) unter Bildung der Titelverbindungen (IV) [analoge Darstellung von (V)‐(VII)].

Reactions of Enolates with Vinyl Selenoxides and Vinyl Selenones. One-step Synthesis of Cyclopropylcarbonyl Compounds

Abstract In the reactions with enolate anions, organoselenium moieties of aryl vinyl selenoxides and selenones have exhibited two important roles, e.g., activation of C=C bonds for conjugate addition reaction and behaviors as excellent leaving groups. Owing to such characteristic features, ketone enolates react with p-chlorophenyl vinyl selenoxide to afford the corresponding cyclopropyl ketones through an initial conjugate addition followed by substitution processes. On the other hand, use of vinyl selenones usually gives much better results with anionic species of active methylene compounds. Vinyl selenones bearing hydroxyl, ketone, and ester groups can also be employed equally well for this type of transformation.

Selenosulfonation of disubstituted acetylenes: reactions of corresponding vinyl selenoxides and anomalous formation of a ketene diselenoacetal

Selenosulfonation de phenyl-1 hexyne-1, trimethylsilyl-1 propyne, et decyne-5 a l'aide du p-tolueneselenosulfonate de Se-phenyle

Organoselenium chemistry. Formation of acetylenes and allenes by syn elimination of vinyl selenoxides

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTOrganoselenium chemistry. Formation of acetylenes and allenes by syn elimination of vinyl selenoxidesHans J. Reich and William W. Willis Jr.Cite this: J. Am. Chem. Soc. 1980, 102, 18, 5967–5968Publication Date (Print):August 1, 1980Publication History Published online1 May 2002Published inissue 1 August 1980https://doi.org/10.1021/ja00538a072RIGHTS & PERMISSIONSArticle Views372Altmetric-Citations39LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (294 KB) Get e-Alerts Get e-Alerts

Synthetic route to vinyl selenides and vinyl selenoxides

Synthetic route to vinyl selenides and vinyl selenoxides