Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways

Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives were investigated. The regioselectivities of these processes were found to be influenced by the structure of cyclopropanols as well as the counter anion of the copper(II) salts. A mechanism involving rear...

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Autores principales: Hasegawa, Eietsu, Tateyama, Minami, Nagumo, Ryosuke, Tayama, Eiji, Iwamoto, Hajime
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3740709/
https://www.ncbi.nlm.nih.gov/pubmed/23946834
http://dx.doi.org/10.3762/bjoc.9.156
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author Hasegawa, Eietsu
Tateyama, Minami
Nagumo, Ryosuke
Tayama, Eiji
Iwamoto, Hajime
author_facet Hasegawa, Eietsu
Tateyama, Minami
Nagumo, Ryosuke
Tayama, Eiji
Iwamoto, Hajime
author_sort Hasegawa, Eietsu
collection PubMed
description Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives were investigated. The regioselectivities of these processes were found to be influenced by the structure of cyclopropanols as well as the counter anion of the copper(II) salts. A mechanism involving rearrangement reactions of radical intermediates and their competitive trapping by copper ions is proposed.
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spelling pubmed-37407092013-08-14 Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways Hasegawa, Eietsu Tateyama, Minami Nagumo, Ryosuke Tayama, Eiji Iwamoto, Hajime Beilstein J Org Chem Full Research Paper Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives were investigated. The regioselectivities of these processes were found to be influenced by the structure of cyclopropanols as well as the counter anion of the copper(II) salts. A mechanism involving rearrangement reactions of radical intermediates and their competitive trapping by copper ions is proposed. Beilstein-Institut 2013-07-11 /pmc/articles/PMC3740709/ /pubmed/23946834 http://dx.doi.org/10.3762/bjoc.9.156 Text en Copyright © 2013, Hasegawa 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
Hasegawa, Eietsu
Tateyama, Minami
Nagumo, Ryosuke
Tayama, Eiji
Iwamoto, Hajime
Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways
title Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways
title_full Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways
title_fullStr Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways
title_full_unstemmed Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways
title_short Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways
title_sort copper(ii)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3740709/
https://www.ncbi.nlm.nih.gov/pubmed/23946834
http://dx.doi.org/10.3762/bjoc.9.156
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