Preparation of SF5 Aromatics by Vicarious Nucleophilic Substitution Reactions of Nitro(pentafluorosulfanyl)benzenes with Carbanions

0360936 - ÚOCHB 2012 RIV US eng J - Journal Article
Beier, Petr - Pastýříková, Tereza - Iakobson, George
Preparation of SF5 Aromatics by Vicarious Nucleophilic Substitution Reactions of Nitro(pentafluorosulfanyl)benzenes with Carbanions.
Journal of Organic Chemistry. Roč. 76, č. 11 (2011), s. 4781-4786. ISSN 0022-3263. E-ISSN 1520-6904
Institutional research plan: CEZ:AV0Z40550506
Keywords : sulfur pentafluorides * vicarious nucleophilic aromatic substitution * nitrobenzenes
Subject RIV: CC - Organic Chemistry
Impact factor: 4.450, year: 2011

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.
Permanent Link: http://hdl.handle.net/11104/0198373