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On the cause of low thermal stability of ethyl halodiazoacetates

Rates for the thermal decomposition of ethyl halodiazoacetates (halo = Cl, Br, I) have been obtained, and reported herein are their half-lives. The experimental results are supported by DFT calculations, and we provide a possible explanation for the reduced thermal stability of ethyl halodiazoacetat...

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Autores principales: Mortén, Magnus, Hennum, Martin, Bonge-Hansen, Tore
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979875/
https://www.ncbi.nlm.nih.gov/pubmed/27559411
http://dx.doi.org/10.3762/bjoc.12.155
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author Mortén, Magnus
Hennum, Martin
Bonge-Hansen, Tore
author_facet Mortén, Magnus
Hennum, Martin
Bonge-Hansen, Tore
author_sort Mortén, Magnus
collection PubMed
description Rates for the thermal decomposition of ethyl halodiazoacetates (halo = Cl, Br, I) have been obtained, and reported herein are their half-lives. The experimental results are supported by DFT calculations, and we provide a possible explanation for the reduced thermal stability of ethyl halodiazoacetates compared to ethyl diazoacetate and for the relative decomposition rates between the chloro, bromo and iodo analogs. We have also briefly studied the thermal, non-catalytic cyclopropanation of styrenes and compared the results to the analogous Rh(II)-catalyzed reactions.
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spelling pubmed-49798752016-08-24 On the cause of low thermal stability of ethyl halodiazoacetates Mortén, Magnus Hennum, Martin Bonge-Hansen, Tore Beilstein J Org Chem Full Research Paper Rates for the thermal decomposition of ethyl halodiazoacetates (halo = Cl, Br, I) have been obtained, and reported herein are their half-lives. The experimental results are supported by DFT calculations, and we provide a possible explanation for the reduced thermal stability of ethyl halodiazoacetates compared to ethyl diazoacetate and for the relative decomposition rates between the chloro, bromo and iodo analogs. We have also briefly studied the thermal, non-catalytic cyclopropanation of styrenes and compared the results to the analogous Rh(II)-catalyzed reactions. Beilstein-Institut 2016-07-26 /pmc/articles/PMC4979875/ /pubmed/27559411 http://dx.doi.org/10.3762/bjoc.12.155 Text en Copyright © 2016, Mortén 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
Mortén, Magnus
Hennum, Martin
Bonge-Hansen, Tore
On the cause of low thermal stability of ethyl halodiazoacetates
title On the cause of low thermal stability of ethyl halodiazoacetates
title_full On the cause of low thermal stability of ethyl halodiazoacetates
title_fullStr On the cause of low thermal stability of ethyl halodiazoacetates
title_full_unstemmed On the cause of low thermal stability of ethyl halodiazoacetates
title_short On the cause of low thermal stability of ethyl halodiazoacetates
title_sort on the cause of low thermal stability of ethyl halodiazoacetates
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979875/
https://www.ncbi.nlm.nih.gov/pubmed/27559411
http://dx.doi.org/10.3762/bjoc.12.155
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