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Dehydration of (Perfluoroalkyl)tetramethylcyclopentenol

(Perfluoroalkyl) tetramethylcyclopentenols (alkyl = n-butyl, n-hexyl, n-octyl) were dehydrated to a complex mixture of endo, endo-(perfluoroalkyl) tetramethyl-cyclopentadienes and their endo-, exo-isomers. It was found in preliminary screening experiments that the best reagent for this transformatio...

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Autores principales: Čermák, Jan, Thi, Thu Huong Nguyen, Včelák, Jaroslav, Krupková, Alena
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263349/
http://dx.doi.org/10.3390/molecules16054031
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author Čermák, Jan
Thi, Thu Huong Nguyen
Včelák, Jaroslav
Krupková, Alena
author_facet Čermák, Jan
Thi, Thu Huong Nguyen
Včelák, Jaroslav
Krupková, Alena
author_sort Čermák, Jan
collection PubMed
description (Perfluoroalkyl) tetramethylcyclopentenols (alkyl = n-butyl, n-hexyl, n-octyl) were dehydrated to a complex mixture of endo, endo-(perfluoroalkyl) tetramethyl-cyclopentadienes and their endo-, exo-isomers. It was found in preliminary screening experiments that the best reagent for this transformation, giving an 89% yield of isomeric product mixture, was P(2)O(5) in benzene at 80-90 °C. Products were characterized on the basis of their mass spectra and retention time information, and some peaks in the mass spectra were identified from their molecular fragments. Structures were assigned to the three most abundant products of (perfluorohexyl)tetramethylcyclopentenol dehydration. Formal dehydration kinetics showed a second order reaction in benzene but zeroth order with induction period in chlorobenzene, suggesting mass transfer limitations in the more polar chlorobenzene. Some of the products were formed by consecutive isomerization of the others, as shown by the kinetic analysis.
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spelling pubmed-62633492018-12-10 Dehydration of (Perfluoroalkyl)tetramethylcyclopentenol Čermák, Jan Thi, Thu Huong Nguyen Včelák, Jaroslav Krupková, Alena Molecules Article (Perfluoroalkyl) tetramethylcyclopentenols (alkyl = n-butyl, n-hexyl, n-octyl) were dehydrated to a complex mixture of endo, endo-(perfluoroalkyl) tetramethyl-cyclopentadienes and their endo-, exo-isomers. It was found in preliminary screening experiments that the best reagent for this transformation, giving an 89% yield of isomeric product mixture, was P(2)O(5) in benzene at 80-90 °C. Products were characterized on the basis of their mass spectra and retention time information, and some peaks in the mass spectra were identified from their molecular fragments. Structures were assigned to the three most abundant products of (perfluorohexyl)tetramethylcyclopentenol dehydration. Formal dehydration kinetics showed a second order reaction in benzene but zeroth order with induction period in chlorobenzene, suggesting mass transfer limitations in the more polar chlorobenzene. Some of the products were formed by consecutive isomerization of the others, as shown by the kinetic analysis. MDPI 2011-05-17 /pmc/articles/PMC6263349/ http://dx.doi.org/10.3390/molecules16054031 Text en © 2011 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Čermák, Jan
Thi, Thu Huong Nguyen
Včelák, Jaroslav
Krupková, Alena
Dehydration of (Perfluoroalkyl)tetramethylcyclopentenol
title Dehydration of (Perfluoroalkyl)tetramethylcyclopentenol
title_full Dehydration of (Perfluoroalkyl)tetramethylcyclopentenol
title_fullStr Dehydration of (Perfluoroalkyl)tetramethylcyclopentenol
title_full_unstemmed Dehydration of (Perfluoroalkyl)tetramethylcyclopentenol
title_short Dehydration of (Perfluoroalkyl)tetramethylcyclopentenol
title_sort dehydration of (perfluoroalkyl)tetramethylcyclopentenol
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263349/
http://dx.doi.org/10.3390/molecules16054031
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