On the cause of low thermal stability of ethyl halodiazoacetates

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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Bibliographic Details
Main Authors: Magnus Mortén, Martin Hennum, Tore Bonge-Hansen
Format: Article
Language:English
Published: Beilstein-Institut 2016-07-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
carbenes
catalysis
cyclopropanation
halo diazoacetates
half-lives
thermal stability
Online Access:https://doi.org/10.3762/bjoc.12.155
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spelling doaj-dd55a86984cd4a069519d539dc5b8fc72021-02-02T08:28:37ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-07-011211590159710.3762/bjoc.12.1551860-5397-12-155On the cause of low thermal stability of ethyl halodiazoacetatesMagnus Mortén0Martin Hennum1Tore Bonge-Hansen2Department of Chemistry, University of Oslo, P.O. Box 1033 Blindern, NO-0315 Oslo, NorwayDepartment of Chemistry, University of Oslo, P.O. Box 1033 Blindern, NO-0315 Oslo, NorwayDepartment of Chemistry, University of Oslo, P.O. Box 1033 Blindern, NO-0315 Oslo, NorwayRates 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.https://doi.org/10.3762/bjoc.12.155carbenescatalysiscyclopropanationhalo diazoacetateshalf-livesthermal stability
collection DOAJ
language English
format Article
sources DOAJ
author Magnus Mortén
Martin Hennum
Tore Bonge-Hansen
spellingShingle Magnus Mortén
Martin Hennum
Tore Bonge-Hansen
On the cause of low thermal stability of ethyl halodiazoacetates
Beilstein Journal of Organic Chemistry
carbenes
catalysis
cyclopropanation
halo diazoacetates
half-lives
thermal stability
author_facet Magnus Mortén
Martin Hennum
Tore Bonge-Hansen
author_sort Magnus Mortén
title On the cause of low thermal stability of ethyl halodiazoacetates
title_short 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_sort on the cause of low thermal stability of ethyl halodiazoacetates
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2016-07-01
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.
topic carbenes
catalysis
cyclopropanation
halo diazoacetates
half-lives
thermal stability
url https://doi.org/10.3762/bjoc.12.155
work_keys_str_mv AT magnusmorten onthecauseoflowthermalstabilityofethylhalodiazoacetates
AT martinhennum onthecauseoflowthermalstabilityofethylhalodiazoacetates
AT torebongehansen onthecauseoflowthermalstabilityofethylhalodiazoacetates
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