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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Royal Society of Chemistry
2018
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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 |
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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
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title_full | Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity
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title_fullStr | Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity
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title_full_unstemmed | Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity
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title_short | Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity
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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 |
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