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Two-Phase Dibromocyclopropanation of Unsaturated Alcohols Using Flow Chemistry

Dibromocyclopropanations are conventionally done by addition of dibromocarbene to alkenes under phase-transfer conditions in batch reactions using a strong base (50% NaOH (aq)), vigorous stirring and long reaction times. We have shown that cyclopropanation of unsaturated alcohols can be done under a...

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Detalles Bibliográficos
Autores principales: Østby, Runa Berg, Didriksen, Terje, Antonsen, Simen Gjelseth, Nicolaisen, Steinar Sollien, Stenstrøm, Yngve
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7288115/
https://www.ncbi.nlm.nih.gov/pubmed/32438720
http://dx.doi.org/10.3390/molecules25102364
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author Østby, Runa Berg
Didriksen, Terje
Antonsen, Simen Gjelseth
Nicolaisen, Steinar Sollien
Stenstrøm, Yngve
author_facet Østby, Runa Berg
Didriksen, Terje
Antonsen, Simen Gjelseth
Nicolaisen, Steinar Sollien
Stenstrøm, Yngve
author_sort Østby, Runa Berg
collection PubMed
description Dibromocyclopropanations are conventionally done by addition of dibromocarbene to alkenes under phase-transfer conditions in batch reactions using a strong base (50% NaOH (aq)), vigorous stirring and long reaction times. We have shown that cyclopropanation of unsaturated alcohols can be done under ambient conditions using continuous flow chemistry with 40% (w/w) NaOH (aq) as the base. The reactions were generally rapid; the yields were comparable to yields reported in the literature for the conventional batch reaction
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spelling pubmed-72881152020-06-17 Two-Phase Dibromocyclopropanation of Unsaturated Alcohols Using Flow Chemistry Østby, Runa Berg Didriksen, Terje Antonsen, Simen Gjelseth Nicolaisen, Steinar Sollien Stenstrøm, Yngve Molecules Article Dibromocyclopropanations are conventionally done by addition of dibromocarbene to alkenes under phase-transfer conditions in batch reactions using a strong base (50% NaOH (aq)), vigorous stirring and long reaction times. We have shown that cyclopropanation of unsaturated alcohols can be done under ambient conditions using continuous flow chemistry with 40% (w/w) NaOH (aq) as the base. The reactions were generally rapid; the yields were comparable to yields reported in the literature for the conventional batch reaction MDPI 2020-05-19 /pmc/articles/PMC7288115/ /pubmed/32438720 http://dx.doi.org/10.3390/molecules25102364 Text en © 2020 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 (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Østby, Runa Berg
Didriksen, Terje
Antonsen, Simen Gjelseth
Nicolaisen, Steinar Sollien
Stenstrøm, Yngve
Two-Phase Dibromocyclopropanation of Unsaturated Alcohols Using Flow Chemistry
title Two-Phase Dibromocyclopropanation of Unsaturated Alcohols Using Flow Chemistry
title_full Two-Phase Dibromocyclopropanation of Unsaturated Alcohols Using Flow Chemistry
title_fullStr Two-Phase Dibromocyclopropanation of Unsaturated Alcohols Using Flow Chemistry
title_full_unstemmed Two-Phase Dibromocyclopropanation of Unsaturated Alcohols Using Flow Chemistry
title_short Two-Phase Dibromocyclopropanation of Unsaturated Alcohols Using Flow Chemistry
title_sort two-phase dibromocyclopropanation of unsaturated alcohols using flow chemistry
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7288115/
https://www.ncbi.nlm.nih.gov/pubmed/32438720
http://dx.doi.org/10.3390/molecules25102364
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