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

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...

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Main Authors:	Norbert Vida, Jiří Václavík, Petr Beier
Format:	Article
Language:	English
Published:	Beilstein-Institut 2016-01-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	dearomatization decarboxylation Diels–Alder reaction oxidation pentafluorosulfanyl group
Online Access:	https://doi.org/10.3762/bjoc.12.12

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spelling	doaj-c1a880b8e3704318944f6a44d955e0f42021-02-02T06:47:35ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-01-0112111011610.3762/bjoc.12.121860-5397-12-12Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenesNorbert Vida0Jiří Václavík1Petr Beier2Institute of Organic Chemistry and Biochemistry, v.v.i., Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech RepublicInstitute of Organic Chemistry and Biochemistry, v.v.i., Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech RepublicInstitute of Organic Chemistry and Biochemistry, v.v.i., Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech RepublicOxidation 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.https://doi.org/10.3762/bjoc.12.12dearomatizationdecarboxylationDiels–Alder reactionoxidationpentafluorosulfanyl group
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Norbert Vida Jiří Václavík Petr Beier
spellingShingle	Norbert Vida Jiří Václavík Petr Beier Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes Beilstein Journal of Organic Chemistry dearomatization decarboxylation Diels–Alder reaction oxidation pentafluorosulfanyl group
author_facet	Norbert Vida Jiří Václavík Petr Beier
author_sort	Norbert Vida
title	Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes
title_short	Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes
title_full	Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes
title_fullStr	Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes
title_full_unstemmed	Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes
title_sort	synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2016-01-01
description	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.
topic	dearomatization decarboxylation Diels–Alder reaction oxidation pentafluorosulfanyl group
url	https://doi.org/10.3762/bjoc.12.12
work_keys_str_mv	AT norbertvida synthesisandreactivityofaliphaticsulfurpentafluoridesfromsubstitutedpentafluorosulfanylbenzenes AT jirivaclavik synthesisandreactivityofaliphaticsulfurpentafluoridesfromsubstitutedpentafluorosulfanylbenzenes AT petrbeier synthesisandreactivityofaliphaticsulfurpentafluoridesfromsubstitutedpentafluorosulfanylbenzenes
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Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes

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