Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide

Cyclopropylacetylene reacts with two molar equivalents of Piers' borane [HB(C(6)F(5))(2)] under mild conditions by an addition/rearrangement sequence with cyclopropyl ring opening to give a mixture of two α-B(C(6)F(5))(2) substituted tetrahydroboroles. This compound forms an active frustrated L...

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Autores principales: Liu, Yun-Lin, Kehr, Gerald, Daniliuc, Constantin G., Erker, Gerhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5369401/
https://www.ncbi.nlm.nih.gov/pubmed/28451249
http://dx.doi.org/10.1039/c6sc03468c
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author Liu, Yun-Lin
Kehr, Gerald
Daniliuc, Constantin G.
Erker, Gerhard
author_facet Liu, Yun-Lin
Kehr, Gerald
Daniliuc, Constantin G.
Erker, Gerhard
author_sort Liu, Yun-Lin
collection PubMed
description Cyclopropylacetylene reacts with two molar equivalents of Piers' borane [HB(C(6)F(5))(2)] under mild conditions by an addition/rearrangement sequence with cyclopropyl ring opening to give a mixture of two α-B(C(6)F(5))(2) substituted tetrahydroboroles. This compound forms an active frustrated Lewis pair with P( t )Bu(3) that heterolytically splits dihydrogen and adds carbon dioxide as a geminal chelate bis-boryl component. The respective reactions of the two-fold HB(C(6)F(5))(2) addition to Ph-CH(2)CH(2)C[triple bond, length as m-dash]CH were studied as a geminal Lewis acid reference. Most of the products were characterized by X-ray diffraction.
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spelling pubmed-53694012017-04-27 Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide Liu, Yun-Lin Kehr, Gerald Daniliuc, Constantin G. Erker, Gerhard Chem Sci Chemistry Cyclopropylacetylene reacts with two molar equivalents of Piers' borane [HB(C(6)F(5))(2)] under mild conditions by an addition/rearrangement sequence with cyclopropyl ring opening to give a mixture of two α-B(C(6)F(5))(2) substituted tetrahydroboroles. This compound forms an active frustrated Lewis pair with P( t )Bu(3) that heterolytically splits dihydrogen and adds carbon dioxide as a geminal chelate bis-boryl component. The respective reactions of the two-fold HB(C(6)F(5))(2) addition to Ph-CH(2)CH(2)C[triple bond, length as m-dash]CH were studied as a geminal Lewis acid reference. Most of the products were characterized by X-ray diffraction. Royal Society of Chemistry 2017-02-01 2016-09-16 /pmc/articles/PMC5369401/ /pubmed/28451249 http://dx.doi.org/10.1039/c6sc03468c Text en This journal is © The Royal Society of Chemistry 2016 https://creativecommons.org/licenses/by/3.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/ (https://creativecommons.org/licenses/by/3.0/) ) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Liu, Yun-Lin
Kehr, Gerald
Daniliuc, Constantin G.
Erker, Gerhard
Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide
title Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide
title_full Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide
title_fullStr Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide
title_full_unstemmed Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide
title_short Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide
title_sort geminal bis-borane formation by borane lewis acid induced cyclopropyl rearrangement and its frustrated lewis pair reaction with carbon dioxide
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5369401/
https://www.ncbi.nlm.nih.gov/pubmed/28451249
http://dx.doi.org/10.1039/c6sc03468c
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