Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides

β-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br(+) and I(+) ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave α-ha...

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Autores principales: Shimizu, Akihiro, Hayashi, Ryutaro, Ashikari, Yosuke, Nokami, Toshiki, Yoshida, Jun-ichi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4362321/
https://www.ncbi.nlm.nih.gov/pubmed/25815076
http://dx.doi.org/10.3762/bjoc.11.27
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author Shimizu, Akihiro
Hayashi, Ryutaro
Ashikari, Yosuke
Nokami, Toshiki
Yoshida, Jun-ichi
author_facet Shimizu, Akihiro
Hayashi, Ryutaro
Ashikari, Yosuke
Nokami, Toshiki
Yoshida, Jun-ichi
author_sort Shimizu, Akihiro
collection PubMed
description β-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br(+) and I(+) ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave α-halocarbonyl compounds.
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spelling pubmed-43623212015-03-26 Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides Shimizu, Akihiro Hayashi, Ryutaro Ashikari, Yosuke Nokami, Toshiki Yoshida, Jun-ichi Beilstein J Org Chem Full Research Paper β-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br(+) and I(+) ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave α-halocarbonyl compounds. Beilstein-Institut 2015-02-13 /pmc/articles/PMC4362321/ /pubmed/25815076 http://dx.doi.org/10.3762/bjoc.11.27 Text en Copyright © 2015, Shimizu 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
Shimizu, Akihiro
Hayashi, Ryutaro
Ashikari, Yosuke
Nokami, Toshiki
Yoshida, Jun-ichi
Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides
title Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides
title_full Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides
title_fullStr Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides
title_full_unstemmed Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides
title_short Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides
title_sort switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4362321/
https://www.ncbi.nlm.nih.gov/pubmed/25815076
http://dx.doi.org/10.3762/bjoc.11.27
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