Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

A series of 1-substituted-3-methyl-2-phospholene oxides was prepared from the corresponding 3-phospholene oxides by double bond rearrangement. The 2-phospholene oxides could be obtained by heating the 3-phospholene oxides in methanesulfonic acid, or via the formation of cyclic chlorophosphonium salt...

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Autores principales: Bagi, Péter, Herbay, Réka, Péczka, Nikolett, Mucsi, Zoltán, Timári, István, Keglevich, and György
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7189000/
https://www.ncbi.nlm.nih.gov/pubmed/32395185
http://dx.doi.org/10.3762/bjoc.16.75
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author Bagi, Péter
Herbay, Réka
Péczka, Nikolett
Mucsi, Zoltán
Timári, István
Keglevich, and György
author_facet Bagi, Péter
Herbay, Réka
Péczka, Nikolett
Mucsi, Zoltán
Timári, István
Keglevich, and György
author_sort Bagi, Péter
collection PubMed
description A series of 1-substituted-3-methyl-2-phospholene oxides was prepared from the corresponding 3-phospholene oxides by double bond rearrangement. The 2-phospholene oxides could be obtained by heating the 3-phospholene oxides in methanesulfonic acid, or via the formation of cyclic chlorophosphonium salts. Whereas mixtures of the 2- and 3-phospholene oxides formed, when the isomerization of 3-phospholene oxides was attempted under thermal conditions, or in the presence of a base. The mechanisms of the various double bond migration pathways were elucidated by quantum chemical calculations.
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spelling pubmed-71890002020-05-11 Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides Bagi, Péter Herbay, Réka Péczka, Nikolett Mucsi, Zoltán Timári, István Keglevich, and György Beilstein J Org Chem Full Research Paper A series of 1-substituted-3-methyl-2-phospholene oxides was prepared from the corresponding 3-phospholene oxides by double bond rearrangement. The 2-phospholene oxides could be obtained by heating the 3-phospholene oxides in methanesulfonic acid, or via the formation of cyclic chlorophosphonium salts. Whereas mixtures of the 2- and 3-phospholene oxides formed, when the isomerization of 3-phospholene oxides was attempted under thermal conditions, or in the presence of a base. The mechanisms of the various double bond migration pathways were elucidated by quantum chemical calculations. Beilstein-Institut 2020-04-22 /pmc/articles/PMC7189000/ /pubmed/32395185 http://dx.doi.org/10.3762/bjoc.16.75 Text en Copyright © 2020, Bagi et al. https://creativecommons.org/licenses/by/4.0https://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/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. 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
Bagi, Péter
Herbay, Réka
Péczka, Nikolett
Mucsi, Zoltán
Timári, István
Keglevich, and György
Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides
title Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides
title_full Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides
title_fullStr Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides
title_full_unstemmed Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides
title_short Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides
title_sort preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7189000/
https://www.ncbi.nlm.nih.gov/pubmed/32395185
http://dx.doi.org/10.3762/bjoc.16.75
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