ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTtert-Butyl [[2-(trimethylsilyl)ethyl]sulfonyl]carbamate: a new reagent for use in Mitsunobu reactionsJeffrey A. Campbell and David J. HartCite this: J. Org. Chem. 1993, 58, 10, 2900–2903Publication Date (Print):May 1, 1993Publication History Published online1 May 2002Published inissue 1 May 1993https://pubs.acs.org/doi/10.1021/jo00062a041https://doi.org/10.1021/jo00062a041research-articleACS PublicationsRequest reuse permissionsArticle Views720Altmetric-Citations63LEARN 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 InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information Get e-Alerts
[36896-63-6] C8H11AlS (MW 166.22) InChI = 1S/C6H6S.2CH3.Al/c7-6-4-2-1-3-5-6;;;/h1-5,7H;2*1H3;/q;;;+1/p-1 InChIKey = OKDMDDDFDCMSSS-UHFFFAOYSA-M (reagent used as a source of nucleophilic phenylthiolate in a wide array of reactions) Solubility: soluble in CH2Cl2, THF, hexane, and benzene. Form Supplied in: generated in situ from commercially available materials. Preparative Methods: to a solution of thiophenol (0.26 g, 2.4 mmol) in CH2Cl2 (2 mL) is added trimethylaluminum (1.0 M solution in hexane, 2.4 mL, 2.4 mmol) at 0 °C under argon. This mixture is kept at 0 °C for 20 min, and then additional reactants are added.1 Purification: Me2AlSPh can be generated, isolated as a solid, and recrystallized from pentane to form colorless plates of polymeric Me2AlSPh.2 Handling, Storage, and Precautions: Me2AlSPh should be generated and handled under an inert gas atmosphere. Stock solutions of this reagent can be stored under refrigeration for long time periods.3 Use of a fume hood is highly recommended.
Abstract Treatment of vinylogous urethanes 9a and 9b with tri‐ n ‐butyl in hydride generated a tree radical that underwent cyclization‐fragmentation to afford oxindole‐ketones 10 and 11 in high yield. Vinylogous urethane 13 , gave only cyclization‐reduction products 15 and 16 upon treatment with tri‐ n ‐butyltin hydride at 80 °C, but also afforded a low yield of cyclization‐fragmentation product 14 upon treatment with tris(trimethyl‐silyl)silane at 140 °C.
Organic chemists have begun to use intra- and intermolecular free-radical addition reactions to develop useful synthetic transformations. Carboncentered radicals can form bonds with electron-rich or electron-deficient alkenes, allenes, and acetylenes. Radical addition reactions can also be used to construct hindered carbon-carbon bonds. These characteristics, as well as the large number of functional groups that tolerate free-radical conditions contribute to the importance of such reactions in organic synthesis.
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