Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene

Under ambient conditions, a [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine 1 with ethylene afforded a bicyclo[2.2.2] derivative 2, which was structurally characterized. The cyclization process was found to be reversible, and thus retro-[4 + 2] cycloaddition reproduced 1 quantitatively, co...

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Autores principales: Wu, Di, Ganguly, Rakesh, Li, Yongxin, Hoo, Sin Ni, Hirao, Hajime, Kinjo, Rei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5952552/
https://www.ncbi.nlm.nih.gov/pubmed/29861951
http://dx.doi.org/10.1039/c5sc03174e
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author Wu, Di
Ganguly, Rakesh
Li, Yongxin
Hoo, Sin Ni
Hirao, Hajime
Kinjo, Rei
author_facet Wu, Di
Ganguly, Rakesh
Li, Yongxin
Hoo, Sin Ni
Hirao, Hajime
Kinjo, Rei
author_sort Wu, Di
collection PubMed
description Under ambient conditions, a [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine 1 with ethylene afforded a bicyclo[2.2.2] derivative 2, which was structurally characterized. The cyclization process was found to be reversible, and thus retro-[4 + 2] cycloaddition reproduced 1 quantitatively, concomitant with the release of ethylene. Compound 1 reacted regio-selectively and stereo-selectively with styrene derivatives and norbornene, respectively, and these processes were found to be reversible too. Computational studies determined the reaction pathways which were consistent with the regio-selectivity observed in the reaction of styrene, and the reaction was suggested to be essentially concerted but highly asynchronous.
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spelling pubmed-59525522018-06-01 Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene Wu, Di Ganguly, Rakesh Li, Yongxin Hoo, Sin Ni Hirao, Hajime Kinjo, Rei Chem Sci Chemistry Under ambient conditions, a [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine 1 with ethylene afforded a bicyclo[2.2.2] derivative 2, which was structurally characterized. The cyclization process was found to be reversible, and thus retro-[4 + 2] cycloaddition reproduced 1 quantitatively, concomitant with the release of ethylene. Compound 1 reacted regio-selectively and stereo-selectively with styrene derivatives and norbornene, respectively, and these processes were found to be reversible too. Computational studies determined the reaction pathways which were consistent with the regio-selectivity observed in the reaction of styrene, and the reaction was suggested to be essentially concerted but highly asynchronous. Royal Society of Chemistry 2015-12-01 2015-09-15 /pmc/articles/PMC5952552/ /pubmed/29861951 http://dx.doi.org/10.1039/c5sc03174e Text en This journal is © The Royal Society of Chemistry 2015 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
Wu, Di
Ganguly, Rakesh
Li, Yongxin
Hoo, Sin Ni
Hirao, Hajime
Kinjo, Rei
Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene
title Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene
title_full Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene
title_fullStr Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene
title_full_unstemmed Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene
title_short Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene
title_sort reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5952552/
https://www.ncbi.nlm.nih.gov/pubmed/29861951
http://dx.doi.org/10.1039/c5sc03174e
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