Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes

0472638 - MBÚ 2017 RIV DE eng J - Journal Article
Vida, N. - Václavík, Jiří - Beier, P.
Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes.
Beilstein Journal of Organic Chemistry. Roč. 12, JAN 20 2016 (2016), s. 110-116. ISSN 1860-5397. E-ISSN 1860-5397
Institutional support: RVO:67985840
Keywords : dearomatization * decarboxylation * Diels-Alder reaction
Subject RIV: EE - Microbiology, Virology
Impact factor: 2.337, year: 2016

Oxidation of 3- and 4-pentafluorosulfanyl-substituted anisoles and phenols with hydrogen peroxide and sulfuric acid provided a mixture of SF5-substituted muconolactone, maleic, and succinic acids. A plausible mechanism for the formation of the aliphatic SF5 compounds was presented and their chemical reactivity was investigated. SF5-substituted para-benzoquinone was synthesized; its oxidation led to an improved yield of 2-(pentafluorosulfanyl)maleic acid. The reaction of SF5-substituted maleic anhydride and para-benzoquinone with cyclopentadiene afforded the Diels-Alder adducts. Decomposition of 3-(pentafluorosulfanyl)muconolactone in acidic, neutral and basic aqueous media was investigated and the decarboxylation of 2-(pentafluorosulfanyl)maleic acid provided 3-(pentafluorosulfanyl)acrylic acid.
Permanent Link: http://hdl.handle.net/11104/0269889