Center for Molecular Modeling - K. Abbaspour Tehrani https://molmod.ugent.be/publication-authors/k-abbaspour-tehrani en Synthesis of 3-Methoxyazetidines via an Aziridine to Azetidine Rearrangement and Theoretical Rationalization of the Reaction Mechanism https://molmod.ugent.be/publications/synthesis-3-methoxyazetidines-aziridine-azetidine-rearrangement-and-theoretical <div class="field field-name-field-a1-authors field-type-taxonomy-term-reference field-label-hidden"> <span class="field-items"> S. Stankovic, S. Catak, M. D&#039;Hooghe, H. Goossens, K. Abbaspour Tehrani, P. Bogaert, M. Waroquier, V. Van Speybroeck, N. De Kimpe </span> </div> <div class="field field-name-field-journal-title field-type-taxonomy-term-reference field-label-hidden"> <span class="field-items"> Journal of Organic Chemistry </span> </div> <div class="field field-name-field-vol-iss field-type-text field-label-hidden"> <div class="field-items"> <div class="field-item even">76 (7), 2157-2167</div> </div> </div> <div class="field field-name-field-a1year field-type-datestamp field-label-hidden"> <div class="field-items"> <div class="field-item even"><span class="date-display-single" property="dc:date" datatype="xsd:dateTime" content="2011-01-01T00:00:00+01:00">2011</span></div> </div> </div> <div class="field field-name-field-a1-type field-type-list-text field-label-hidden"> <div class="field-items"> <div class="field-item even">A1</div> </div> </div> <div class="field field-name-body field-type-text-with-summary field-label-above"> <h3><div class="field-label">Abstract&nbsp;</div></h3> <div class="field-items"> <div class="field-item even" property="content:encoded"><div class="tex2jax"><p>The synthetic utility of N-alkylidene-(2,3-dibromo-2-methylpropyl)amines and N-(2,3-dibromo-2-methylpropylidene)benzylamines was demonstrated by the unexpected synthesis of 3-methoxy-3-methylazetidines upon treatment with sodium borohydride in methanol under reflux through a rare aziridine to azetidine rearrangement. These findings stand in contrast to the known reactivity of the closely related N-alkylidene-(2,3-dibromopropyl)amines, which are easily converted into 2-(bromomethyl)aziridines under the same reaction conditions. A thorough insight into the reaction mechanism was provided by both experimental study and theoretical rationalization.</p> </div></div> </div> </div> <div class="field field-name-field-open-access field-type-list-boolean field-label-hidden"> <div class="field-items"> <div class="field-item even"></div> </div> </div> <div class="field field-name-field-doi field-type-text field-label-above"> <h3><div class="field-label">DOI&nbsp;</div></h3> <div class="field-items"> <div class="field-item even"><div class="tex2jax"><p><a href="http://dx.doi.org/10.1021/jo102555r">http://dx.doi.org/10.1021/jo102555r</a></p> </div></div> </div> </div> <div class="field field-name-field-a1-file field-type-file field-label-above"> <h3><div class="field-label">Private attachment&nbsp;</div></h3> <div class="field-items"> <div class="field-item even"><span class="file"><img class="file-icon" alt="PDF icon" title="application/pdf" src="/modules/file/icons/application-pdf.png" /> <a href="https://molmod.ugent.be/system/files/11%20j.%20org.%20chem.%2076%2C2157%20stankovic.pdf" type="application/pdf; length=2646464">11 j. org. chem. 76,2157 stankovic.pdf</a></span></div> </div> </div> Mon, 22 Aug 2011 14:38:15 +0000 wim 85 at https://molmod.ugent.be https://molmod.ugent.be/publications/synthesis-3-methoxyazetidines-aziridine-azetidine-rearrangement-and-theoretical#comments Selective Transformation of 2-Bromomethyl-2-Methylaziridines to Functionalized Aziridines and Azetidines https://molmod.ugent.be/c1_c3_publications/selective-transformation-2-bromomethyl-2-methylaziridines-functionalized <div class="field field-name-field-a1-authors field-type-taxonomy-term-reference field-label-hidden"> <span class="field-items"> <a href="/publication-authors/s-stankovic" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">S. Stankovic</a>, <a href="/publication-authors/m-dhooghe" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">M. D&#039;Hooghe</a>, <a href="/publication-authors/s-catak" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">S. Catak</a>, <a href="/publication-authors/h-goossens" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">H. Goossens</a>, <a href="/publication-authors/m-waroquier" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">M. Waroquier</a>, <a href="/publication-authors/v-van-speybroeck" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">V. Van Speybroeck</a>, <a href="/publication-authors/k-abbaspour-tehrani" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">K. Abbaspour Tehrani</a>, <a href="/publication-authors/n-de-kimpe" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">N. De Kimpe</a> </span> </div> <div class="field field-name-field-abstract-page field-type-text field-label-hidden"> <div class="field-items"> <div class="field-item even">p.315</div> </div> </div> <div class="field field-name-field-poster-or-talk field-type-list-text field-label-hidden"> <div class="field-items"> <div class="field-item even">Poster</div> </div> </div> <div class="field field-name-field-conference-name field-type-text field-label-above"> <h3><div class="field-label">Conference / event / venue&nbsp;</div></h3> <div class="field-items"> <div class="field-item even">BOSS XIII - Belgian Organic Synthesis Symposium</div> </div> </div> <div class="field field-name-field-conference-location field-type-text field-label-hidden"> <div class="field-items"> <div class="field-item even">KU Leuven Belgium</div> </div> </div> <div class="field field-name-field-conference-dates field-type-date field-label-hidden"> <div class="field-items"> <div class="field-item even"><span class="date-display-range"><span class="date-display-start" property="dc:date" datatype="xsd:dateTime" content="2012-07-15T00:00:00+02:00">Sunday, 15 July, 2012</span> to <span class="date-display-end" property="dc:date" datatype="xsd:dateTime" content="2012-07-20T00:00:00+02:00">Friday, 20 July, 2012</span></span></div> </div> </div> <div class="field field-name-field-abstract-private field-type-file field-label-above"> <h3><div class="field-label">Abstract (private)&nbsp;</div></h3> <div class="field-items"> <div class="field-item even"><span class="file"><img class="file-icon" alt="PDF icon" title="application/pdf" src="/modules/file/icons/application-pdf.png" /> <a href="https://molmod.ugent.be/system/files/abstract%20BOSS%20XIII-Sonja%20Stankovic.pdf" type="application/pdf; length=49244">abstract BOSS XIII-Sonja Stankovic.pdf</a></span></div> </div> </div> Mon, 13 Aug 2012 14:32:49 +0000 catak 1399 at https://molmod.ugent.be https://molmod.ugent.be/c1_c3_publications/selective-transformation-2-bromomethyl-2-methylaziridines-functionalized#comments Selective Transformation of 2-Halomethyl-2-Methylaziridines to Functionalized Aziridines and Azetidines https://molmod.ugent.be/c1_c3_publications/selective-transformation-2-halomethyl-2-methylaziridines-functionalized <div class="field field-name-field-a1-authors field-type-taxonomy-term-reference field-label-hidden"> <span class="field-items"> <a href="/publication-authors/s-stankovic" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">S. Stankovic</a>, <a href="/publication-authors/m-dhooghe" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">M. D&#039;Hooghe</a>, <a href="/publication-authors/s-catak" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">S. Catak</a>, <a href="/publication-authors/h-goossens" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">H. Goossens</a>, <a href="/publication-authors/m-waroquier" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">M. Waroquier</a>, <a href="/publication-authors/v-van-speybroeck" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">V. Van Speybroeck</a>, <a href="/publication-authors/k-abbaspour-tehrani" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">K. Abbaspour Tehrani</a>, <a href="/publication-authors/n-de-kimpe" typeof="skos:Concept" property="rdfs:label skos:prefLabel" datatype="">N. De Kimpe</a> </span> </div> <div class="field field-name-field-abstract-page field-type-text field-label-hidden"> <div class="field-items"> <div class="field-item even">p. 71</div> </div> </div> <div class="field field-name-field-poster-or-talk field-type-list-text field-label-hidden"> <div class="field-items"> <div class="field-item even">Poster</div> </div> </div> <div class="field field-name-field-conference-name field-type-text field-label-above"> <h3><div class="field-label">Conference / event / venue&nbsp;</div></h3> <div class="field-items"> <div class="field-item even">15th Sigma-Aldrich Organic Synthesis Meeting</div> </div> </div> <div class="field field-name-field-conference-location field-type-text field-label-hidden"> <div class="field-items"> <div class="field-item even">Spa, Belgium</div> </div> </div> <div class="field field-name-field-conference-dates field-type-date field-label-hidden"> <div class="field-items"> <div class="field-item even"><span class="date-display-range"><span class="date-display-start" property="dc:date" datatype="xsd:dateTime" content="2011-12-01T00:00:00+01:00">Thursday, 1 December, 2011</span> to <span class="date-display-end" property="dc:date" datatype="xsd:dateTime" content="2011-12-02T00:00:00+01:00">Friday, 2 December, 2011</span></span></div> </div> </div> <div class="field field-name-field-thesis-attachement field-type-file field-label-above"> <h3><div class="field-label">Abstract&nbsp;</div></h3> <div class="field-items"> <div class="field-item even"><span class="file"><img class="file-icon" alt="PDF icon" title="application/pdf" src="/modules/file/icons/application-pdf.png" /> <a href="//molmod.ugent.be/sites/default/files/view.pdf" type="application/pdf; length=47419">view.pdf</a></span></div> </div> </div> Fri, 09 Dec 2011 19:30:10 +0000 catak 930 at https://molmod.ugent.be https://molmod.ugent.be/c1_c3_publications/selective-transformation-2-halomethyl-2-methylaziridines-functionalized#comments