Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts

Through direct transmetalation reaction of Z-vinylic tellurides with nBuLi was observed the unexpected isomerization of double bonds leading to potassium E-vinyltrifluoroborates salts in low to moderate yields. Using EPR spin trapping experiments the radical species that promoted the stereoinversion...

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Autores principales: Stefani, Hélio A, Guadagnin, Rafael C, Keppler, Artur F, Botteselle, Giancarlo V, Comasseto, João V, Suganuma, Carlos A
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2008
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2244621/
https://www.ncbi.nlm.nih.gov/pubmed/18252005
http://dx.doi.org/10.1186/1860-5397-4-9
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author Stefani, Hélio A
Guadagnin, Rafael C
Keppler, Artur F
Botteselle, Giancarlo V
Comasseto, João V
Suganuma, Carlos A
author_facet Stefani, Hélio A
Guadagnin, Rafael C
Keppler, Artur F
Botteselle, Giancarlo V
Comasseto, João V
Suganuma, Carlos A
author_sort Stefani, Hélio A
collection PubMed
description Through direct transmetalation reaction of Z-vinylic tellurides with nBuLi was observed the unexpected isomerization of double bonds leading to potassium E-vinyltrifluoroborates salts in low to moderate yields. Using EPR spin trapping experiments the radical species that promoted the stereoinversion of Z-vinylic organometallic species during the preparation of potassium vinyltrifluoroborate salts was identified. The experiments support the proposed mechanism, which is based on the homolytic cleavage of the TenBu bond.
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spelling pubmed-22446212008-02-15 Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts Stefani, Hélio A Guadagnin, Rafael C Keppler, Artur F Botteselle, Giancarlo V Comasseto, João V Suganuma, Carlos A Beilstein J Org Chem Full Research Paper Through direct transmetalation reaction of Z-vinylic tellurides with nBuLi was observed the unexpected isomerization of double bonds leading to potassium E-vinyltrifluoroborates salts in low to moderate yields. Using EPR spin trapping experiments the radical species that promoted the stereoinversion of Z-vinylic organometallic species during the preparation of potassium vinyltrifluoroborate salts was identified. The experiments support the proposed mechanism, which is based on the homolytic cleavage of the TenBu bond. Beilstein-Institut 2008-02-05 /pmc/articles/PMC2244621/ /pubmed/18252005 http://dx.doi.org/10.1186/1860-5397-4-9 Text en Copyright © 2008, Stefani et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Stefani, Hélio A
Guadagnin, Rafael C
Keppler, Artur F
Botteselle, Giancarlo V
Comasseto, João V
Suganuma, Carlos A
Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
title Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
title_full Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
title_fullStr Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
title_full_unstemmed Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
title_short Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
title_sort mechanistic aspects of the isomerization of z-vinylic tellurides double bonds in the synthesis of potassium z-vinyltrifluoroborate salts
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2244621/
https://www.ncbi.nlm.nih.gov/pubmed/18252005
http://dx.doi.org/10.1186/1860-5397-4-9
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