Cargando…

Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity

The self-stabilizing, tetrameric cyanoborylene [(cAAC)B(CN)](4) (I, cAAC = 1-(2,6-diisopropylphenyl)-3,3,5,5-tetramethylpyrrolidin-2-ylidene) and its diborene relative, [(cAAC)(CN)B[double bond, length as m-dash]B(CN)(cAAC)] (II), both react with disulfides and diselenides to yield the corresponding...

Descripción completa

Detalles Bibliográficos
Autores principales: Auerhammer, Dominic, Arrowsmith, Merle, Dewhurst, Rian D., Kupfer, Thomas, Böhnke, Julian, Braunschweig, Holger
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5897878/
https://www.ncbi.nlm.nih.gov/pubmed/29719698
http://dx.doi.org/10.1039/c7sc04789d
_version_ 1783314028578209792
author Auerhammer, Dominic
Arrowsmith, Merle
Dewhurst, Rian D.
Kupfer, Thomas
Böhnke, Julian
Braunschweig, Holger
author_facet Auerhammer, Dominic
Arrowsmith, Merle
Dewhurst, Rian D.
Kupfer, Thomas
Böhnke, Julian
Braunschweig, Holger
author_sort Auerhammer, Dominic
collection PubMed
description The self-stabilizing, tetrameric cyanoborylene [(cAAC)B(CN)](4) (I, cAAC = 1-(2,6-diisopropylphenyl)-3,3,5,5-tetramethylpyrrolidin-2-ylidene) and its diborene relative, [(cAAC)(CN)B[double bond, length as m-dash]B(CN)(cAAC)] (II), both react with disulfides and diselenides to yield the corresponding cAAC-supported cyanoboron bis(chalcogenides). Furthermore, reactions of I or II with elemental sulfur and selenium in various stoichiometries provided access to a variety of cAAC-stabilized cyanoboron–chalcogen heterocycles, including a unique dithiaborirane, a diboraselenirane, 1,3-dichalcogena-2,4-diboretanes, 1,3,4-trichalcogena-2,5-diborolanes and a rare six-membered 1,2,4,5-tetrathia-3,6-diborinane. Stepwise addition reactions and solution stability studies provided insights into the mechanism of these reactions and the subtle differences in reactivity observed between I and II.
format Online
Article
Text
id pubmed-5897878
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-58978782018-05-01 Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity Auerhammer, Dominic Arrowsmith, Merle Dewhurst, Rian D. Kupfer, Thomas Böhnke, Julian Braunschweig, Holger Chem Sci Chemistry The self-stabilizing, tetrameric cyanoborylene [(cAAC)B(CN)](4) (I, cAAC = 1-(2,6-diisopropylphenyl)-3,3,5,5-tetramethylpyrrolidin-2-ylidene) and its diborene relative, [(cAAC)(CN)B[double bond, length as m-dash]B(CN)(cAAC)] (II), both react with disulfides and diselenides to yield the corresponding cAAC-supported cyanoboron bis(chalcogenides). Furthermore, reactions of I or II with elemental sulfur and selenium in various stoichiometries provided access to a variety of cAAC-stabilized cyanoboron–chalcogen heterocycles, including a unique dithiaborirane, a diboraselenirane, 1,3-dichalcogena-2,4-diboretanes, 1,3,4-trichalcogena-2,5-diborolanes and a rare six-membered 1,2,4,5-tetrathia-3,6-diborinane. Stepwise addition reactions and solution stability studies provided insights into the mechanism of these reactions and the subtle differences in reactivity observed between I and II. Royal Society of Chemistry 2018-01-04 /pmc/articles/PMC5897878/ /pubmed/29719698 http://dx.doi.org/10.1039/c7sc04789d Text en This journal is © The Royal Society of Chemistry 2018 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Auerhammer, Dominic
Arrowsmith, Merle
Dewhurst, Rian D.
Kupfer, Thomas
Böhnke, Julian
Braunschweig, Holger
Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity
title Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity
title_full Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity
title_fullStr Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity
title_full_unstemmed Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity
title_short Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity
title_sort closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5897878/
https://www.ncbi.nlm.nih.gov/pubmed/29719698
http://dx.doi.org/10.1039/c7sc04789d
work_keys_str_mv AT auerhammerdominic closelyrelatedyetdifferentaboryleneanditsdimerarenoninterconvertiblebutconnectedthroughreactivity
AT arrowsmithmerle closelyrelatedyetdifferentaboryleneanditsdimerarenoninterconvertiblebutconnectedthroughreactivity
AT dewhurstriand closelyrelatedyetdifferentaboryleneanditsdimerarenoninterconvertiblebutconnectedthroughreactivity
AT kupferthomas closelyrelatedyetdifferentaboryleneanditsdimerarenoninterconvertiblebutconnectedthroughreactivity
AT bohnkejulian closelyrelatedyetdifferentaboryleneanditsdimerarenoninterconvertiblebutconnectedthroughreactivity
AT braunschweigholger closelyrelatedyetdifferentaboryleneanditsdimerarenoninterconvertiblebutconnectedthroughreactivity