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Preparation of SF5 Aromatics by Vicarious Nucleophilic Substitution Reactions of Nitro(pentafluorosulfanyl)benzenes with Carbanions
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SYSNO ASEP 0360936 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Preparation of SF5 Aromatics by Vicarious Nucleophilic Substitution Reactions of Nitro(pentafluorosulfanyl)benzenes with Carbanions Author(s) Beier, Petr (UOCHB-X) RID, ORCID
Pastýříková, Tereza (UOCHB-X) RID
Iakobson, George (UOCHB-X) RIDNumber of authors 3 Source Title Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 76, č. 11 (2011), s. 4781-4786Number of pages 6 s. Language eng - English Country US - United States Keywords sulfur pentafluorides ; vicarious nucleophilic aromatic substitution ; nitrobenzenes Subject RIV CC - Organic Chemistry CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000291128300055 DOI 10.1021/jo200618p Annotation Vicarious nucleophilic substitutions (VNS) of hydrogen in 1-nitro-4-(pentafluorosulfanyl)benzene with carbanions provide 2-substituted 1-nitro-4-(pentafluorosulfanyl)benzenes in good to high yields. VNS of 1-nitro-3-(pentafluorosulfanyl)benzene gives a mixture of 6- and 4-substituted 1-nitro-3-(pentafluorosulfanyl)benzenes in 85:15 to >98:2 ratio and good to high yields. In basic media, the VNS reactions lead to the formation of carbanions that can be alkylated by alkyl halides affording the corresponding alkylated products in moderate yields. Transformation of primary products to substituted (pentafluorosulfanyl)anilines and 3- or 4-substituted (pentafluorosulfanyl)benzenes is also described. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2012
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