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Conjugated 1,2- and 1,4-Nitrothio(sulfonyl)alkenes and -Dienes

 

作者: Z.F. Pavlova,   E.S. Lipina,   V.V. Perekalin,  

 

期刊: Sulfur reports  (Taylor Available online 1995)
卷期: Volume 16, issue 2  

页码: 149-170

 

ISSN:0196-1772

 

年代: 1995

 

DOI:10.1080/01961779508048737

 

出版商: Taylor & Francis Group

 

关键词: Nitrothioethenes;nitrothiodienes;nitrosulfonylethenes;nitrosulfonyldienes

 

数据来源: Taylor

 

摘要:

The synthesis and reactions of four groups of conjugated sulfur-containing compounds; i.e. 1-nitro-2(4)-thioethenes (and -dienes) and 1-nitro-2(4)-sulfonylethenes (and -dienes), which have become known in recent years, are discussed. Nitrothioethenes may be obtained by elimination reactions of nitrothioketals (synthesised from α-nitro ketones) and nitrohalothioethanes (synthesized from α-nitro-β-acetoxyethanes), as well as by halogen or nitro group displacement by a thio group in 1-nitro-2-halo- or 1,2-dinitroethenes. The last method was used for nitrothiodiene preparation from dinitrodienes. The stereochemistry of the thiylation of conjugated dinitro compounds is described. Nitrosulfonylethenes and -dienes can be obtained by oxidation of the corresponding nitro sulfides as well as by nitrovinylation of arenesulfinates with dinitroethenes and -dienes. Two-electron oxidation of 1-nitro-2-sulfonylethane dianions is suitable for the preparation of 1-nitro-2-sulfonylethenes. Nucleophilic displacement of the sulfur-containing group in nitrothio(sulfonyl)ethenes by amines, alkoxide and thiolate ions as well as Diels-Alder reactions are described. The spectral data (1H NMR, IR, UV) of the compounds mentioned are discussed.

 

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