Radical Cyclisation of α-Halo Aluminium Acetals: A Mechanistic Study.
Identifieur interne : 001853 ( Main/Exploration ); précédent : 001852; suivant : 001854Radical Cyclisation of α-Halo Aluminium Acetals: A Mechanistic Study.
Auteurs : Romain Bénéteau [France] ; Anne Boussonnière [France] ; Jean-Christophe Rouaud [France] ; Jacques Lebreton [France] ; Jérôme Graton [France] ; Denis Jacquemin [France] ; Muriel Sebban [France] ; Hassan Oulyadi [France] ; Ghanem Hamdoun [France] ; Amber N. Hancock [Australie] ; Carl H. Schiesser [Australie] ; Fabrice Dénès [France]Source :
- Chemistry (Weinheim an der Bergstrasse, Germany) [ 1521-3765 ] ; 2016.
Abstract
α-Bromo aluminium acetals are suitable substrates for Ueno-Stork-like radical cyclisations affording γ-lactols and acid-sensitive methylene-γ-lactols in high yields. The mechanistic study herein sets the scope and limitation of this reaction. The influence of the halide (or chalcogenide) atom X (X=Cl, Br, I, SPh, SePh) in the precursors α-haloesters, as well as influence of the solvent and temperature was studied. The structure of the aluminium acetal intermediates resulting from the reduction of the corresponding α-haloesters has been investigated by low-temperature (13) C-INEPT diffusion-ordered NMR spectroscopy (DOSY) experiments and quantum calculations, providing new insights into the structures of these thermally labile intermediates. Oxygen-bridged dimeric structures with a planar Al2 O2 ring are proposed for the least hindered aluminium acetals, while monomeric structures seem to prevail for the most hindered species. A comparison against the radical cyclisation of aluminium acetals derived from allyl and propargyl alcohols with the parent Ueno-Stork has been made at the BHandHLYP/6-311++G(d,p) level of theory, highlighting mechanistic similarities and differences.
DOI: 10.1002/chem.201504780
PubMed: 26890896
Affiliations:
- Australie, France
- Pays de la Loire, Victoria (État)
- Melbourne, Nantes
- Université de Melbourne, Université de Nantes
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UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssinière BP, 92208-44322, Nantes Cedex 3, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>CEISAM UMR 6230 - UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssinière BP, 92208-44322, Nantes Cedex 3</wicri:regionArea><wicri:noRegion>44322, Nantes Cedex 3</wicri:noRegion><orgName type="university">Université de Nantes</orgName><placeName><settlement type="city">Nantes</settlement><region type="region" nuts="2">Pays de la Loire</region></placeName></affiliation></author><author><name sortKey="Graton, Jerome" sort="Graton, Jerome" uniqKey="Graton J" first="Jérôme" last="Graton">Jérôme Graton</name><affiliation wicri:level="4"><nlm:affiliation>CEISAM UMR 6230 - UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssinière BP, 92208-44322, Nantes Cedex 3, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>CEISAM UMR 6230 - UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssinière BP, 92208-44322, Nantes Cedex 3</wicri:regionArea><wicri:noRegion>44322, Nantes Cedex 3</wicri:noRegion><orgName type="university">Université de Nantes</orgName><placeName><settlement type="city">Nantes</settlement><region type="region" nuts="2">Pays de la Loire</region></placeName></affiliation></author><author><name sortKey="Jacquemin, Denis" sort="Jacquemin, Denis" uniqKey="Jacquemin D" first="Denis" last="Jacquemin">Denis Jacquemin</name><affiliation wicri:level="4"><nlm:affiliation>CEISAM UMR 6230 - UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssinière BP, 92208-44322, Nantes Cedex 3, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>CEISAM UMR 6230 - UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssinière BP, 92208-44322, Nantes Cedex 3</wicri:regionArea><wicri:noRegion>44322, Nantes Cedex 3</wicri:noRegion><orgName type="university">Université de Nantes</orgName><placeName><settlement type="city">Nantes</settlement><region type="region" nuts="2">Pays de la Loire</region></placeName></affiliation></author><author><name sortKey="Sebban, Muriel" sort="Sebban, Muriel" uniqKey="Sebban M" first="Muriel" last="Sebban">Muriel Sebban</name><affiliation wicri:level="1"><nlm:affiliation>Normandie Université, COBRA UMR6014, FR3038, Université de Rouen; INSA de Rouen; CNRS, 76821, Mont-Saint-Aignan Cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Normandie Université, COBRA UMR6014, FR3038, Université de Rouen; INSA de Rouen; CNRS, 76821, Mont-Saint-Aignan Cedex</wicri:regionArea><wicri:noRegion>76821, Mont-Saint-Aignan Cedex</wicri:noRegion><wicri:noRegion>76821, Mont-Saint-Aignan Cedex</wicri:noRegion></affiliation></author><author><name sortKey="Oulyadi, Hassan" sort="Oulyadi, Hassan" uniqKey="Oulyadi H" first="Hassan" last="Oulyadi">Hassan Oulyadi</name><affiliation wicri:level="1"><nlm:affiliation>Normandie Université, COBRA UMR6014, FR3038, Université de Rouen; INSA de Rouen; CNRS, 76821, Mont-Saint-Aignan Cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Normandie Université, COBRA UMR6014, FR3038, Université de Rouen; INSA de Rouen; CNRS, 76821, Mont-Saint-Aignan Cedex</wicri:regionArea><wicri:noRegion>76821, Mont-Saint-Aignan Cedex</wicri:noRegion><wicri:noRegion>76821, Mont-Saint-Aignan Cedex</wicri:noRegion></affiliation></author><author><name sortKey="Hamdoun, Ghanem" sort="Hamdoun, Ghanem" uniqKey="Hamdoun G" first="Ghanem" last="Hamdoun">Ghanem Hamdoun</name><affiliation wicri:level="1"><nlm:affiliation>Normandie Université, COBRA UMR6014, FR3038, Université de Rouen; INSA de Rouen; CNRS, 76821, Mont-Saint-Aignan Cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Normandie Université, COBRA UMR6014, FR3038, Université de Rouen; INSA de Rouen; CNRS, 76821, Mont-Saint-Aignan Cedex</wicri:regionArea><wicri:noRegion>76821, Mont-Saint-Aignan Cedex</wicri:noRegion><wicri:noRegion>76821, Mont-Saint-Aignan Cedex</wicri:noRegion></affiliation></author><author><name sortKey="Hancock, Amber N" sort="Hancock, Amber N" uniqKey="Hancock A" first="Amber N" last="Hancock">Amber N. Hancock</name><affiliation wicri:level="4"><nlm:affiliation>School of Chemistry and, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, 3010, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry and, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, 3010</wicri:regionArea><orgName type="university">Université de Melbourne</orgName><placeName><settlement type="city">Melbourne</settlement><region type="état">Victoria (État)</region></placeName></affiliation></author><author><name sortKey="Schiesser, Carl H" sort="Schiesser, Carl H" uniqKey="Schiesser C" first="Carl H" last="Schiesser">Carl H. Schiesser</name><affiliation wicri:level="4"><nlm:affiliation>School of Chemistry and, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, 3010, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry and, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, 3010</wicri:regionArea><orgName type="university">Université de Melbourne</orgName><placeName><settlement type="city">Melbourne</settlement><region type="état">Victoria (État)</region></placeName></affiliation></author><author><name sortKey="Denes, Fabrice" sort="Denes, Fabrice" uniqKey="Denes F" first="Fabrice" last="Dénès">Fabrice Dénès</name><affiliation wicri:level="4"><nlm:affiliation>CEISAM UMR 6230 - UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssinière BP, 92208-44322, Nantes Cedex 3, France. fabrice.denes@univ-nantes.fr.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>CEISAM UMR 6230 - UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssinière BP, 92208-44322, Nantes Cedex 3</wicri:regionArea><wicri:noRegion>44322, Nantes Cedex 3</wicri:noRegion><orgName type="university">Université de Nantes</orgName><placeName><settlement type="city">Nantes</settlement><region type="region" nuts="2">Pays de la Loire</region></placeName></affiliation></author></analytic><series><title level="j">Chemistry (Weinheim an der Bergstrasse, Germany)</title><idno type="eISSN">1521-3765</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">α-Bromo aluminium acetals are suitable substrates for Ueno-Stork-like radical cyclisations affording γ-lactols and acid-sensitive methylene-γ-lactols in high yields. The mechanistic study herein sets the scope and limitation of this reaction. The influence of the halide (or chalcogenide) atom X (X=Cl, Br, I, SPh, SePh) in the precursors α-haloesters, as well as influence of the solvent and temperature was studied. The structure of the aluminium acetal intermediates resulting from the reduction of the corresponding α-haloesters has been investigated by low-temperature (13) C-INEPT diffusion-ordered NMR spectroscopy (DOSY) experiments and quantum calculations, providing new insights into the structures of these thermally labile intermediates. Oxygen-bridged dimeric structures with a planar Al2 O2 ring are proposed for the least hindered aluminium acetals, while monomeric structures seem to prevail for the most hindered species. A comparison against the radical cyclisation of aluminium acetals derived from allyl and propargyl alcohols with the parent Ueno-Stork has been made at the BHandHLYP/6-311++G(d,p) level of theory, highlighting mechanistic similarities and differences.</div></front></TEI><affiliations><list><country><li>Australie</li><li>France</li></country><region><li>Pays de la Loire</li><li>Victoria (État)</li></region><settlement><li>Melbourne</li><li>Nantes</li></settlement><orgName><li>Université de Melbourne</li><li>Université de Nantes</li></orgName></list><tree><country name="France"><region name="Pays de la Loire"><name sortKey="Beneteau, Romain" sort="Beneteau, Romain" uniqKey="Beneteau R" first="Romain" last="Bénéteau">Romain Bénéteau</name></region><name sortKey="Boussonniere, Anne" sort="Boussonniere, Anne" uniqKey="Boussonniere A" first="Anne" last="Boussonnière">Anne Boussonnière</name><name sortKey="Denes, Fabrice" sort="Denes, Fabrice" uniqKey="Denes F" first="Fabrice" last="Dénès">Fabrice Dénès</name><name sortKey="Graton, Jerome" sort="Graton, Jerome" uniqKey="Graton J" first="Jérôme" last="Graton">Jérôme Graton</name><name sortKey="Hamdoun, Ghanem" sort="Hamdoun, Ghanem" uniqKey="Hamdoun G" first="Ghanem" last="Hamdoun">Ghanem Hamdoun</name><name sortKey="Jacquemin, Denis" sort="Jacquemin, Denis" uniqKey="Jacquemin D" first="Denis" last="Jacquemin">Denis Jacquemin</name><name sortKey="Lebreton, Jacques" sort="Lebreton, Jacques" uniqKey="Lebreton J" first="Jacques" last="Lebreton">Jacques Lebreton</name><name sortKey="Oulyadi, Hassan" sort="Oulyadi, Hassan" uniqKey="Oulyadi H" first="Hassan" last="Oulyadi">Hassan Oulyadi</name><name sortKey="Rouaud, Jean Christophe" sort="Rouaud, Jean Christophe" uniqKey="Rouaud J" first="Jean-Christophe" last="Rouaud">Jean-Christophe Rouaud</name><name sortKey="Sebban, Muriel" sort="Sebban, Muriel" uniqKey="Sebban M" first="Muriel" last="Sebban">Muriel Sebban</name></country><country name="Australie"><region name="Victoria (État)"><name sortKey="Hancock, Amber N" sort="Hancock, Amber N" uniqKey="Hancock A" first="Amber N" last="Hancock">Amber N. Hancock</name></region><name sortKey="Schiesser, Carl H" sort="Schiesser, Carl H" uniqKey="Schiesser C" first="Carl H" last="Schiesser">Carl H. Schiesser</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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