Radical Cyclisation of α-Halo Aluminium Acetals: A Mechanistic Study.
Identifieur interne : 002167 ( PubMed/Curation ); précédent : 002166; suivant : 002168Radical 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
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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></affiliation></author><author><name sortKey="Boussonniere, Anne" sort="Boussonniere, Anne" uniqKey="Boussonniere A" first="Anne" last="Boussonnière">Anne Boussonnière</name><affiliation wicri:level="1"><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></affiliation></author><author><name sortKey="Rouaud, Jean Christophe" sort="Rouaud, Jean Christophe" uniqKey="Rouaud J" first="Jean-Christophe" last="Rouaud">Jean-Christophe Rouaud</name><affiliation wicri:level="1"><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></affiliation></author><author><name sortKey="Lebreton, Jacques" sort="Lebreton, Jacques" uniqKey="Lebreton J" first="Jacques" last="Lebreton">Jacques Lebreton</name><affiliation wicri:level="1"><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></affiliation></author><author><name sortKey="Graton, Jerome" sort="Graton, Jerome" uniqKey="Graton J" first="Jérôme" last="Graton">Jérôme Graton</name><affiliation wicri:level="1"><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></affiliation></author><author><name sortKey="Jacquemin, Denis" sort="Jacquemin, Denis" uniqKey="Jacquemin D" first="Denis" last="Jacquemin">Denis Jacquemin</name><affiliation wicri:level="1"><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></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></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></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></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="1"><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></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="1"><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></affiliation></author><author><name sortKey="Denes, Fabrice" sort="Denes, Fabrice" uniqKey="Denes F" first="Fabrice" last="Dénès">Fabrice Dénès</name><affiliation wicri:level="1"><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></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><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">26890896</PMID><DateCreated><Year>2016</Year><Month>03</Month><Day>21</Day></DateCreated><DateCompleted><Year>2016</Year><Month>07</Month><Day>20</Day></DateCompleted><DateRevised><Year>2016</Year><Month>03</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1521-3765</ISSN><JournalIssue CitedMedium="Internet"><Volume>22</Volume><Issue>14</Issue><PubDate><Year>2016</Year><Month>Mar</Month><Day>24</Day></PubDate></JournalIssue><Title>Chemistry (Weinheim an der Bergstrasse, Germany)</Title><ISOAbbreviation>Chemistry</ISOAbbreviation></Journal><ArticleTitle>Radical Cyclisation of α-Halo Aluminium Acetals: A Mechanistic Study.</ArticleTitle><Pagination><MedlinePgn>4809-24</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1002/chem.201504780</ELocationID><Abstract><AbstractText>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.</AbstractText><CopyrightInformation>© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Bénéteau</LastName><ForeName>Romain</ForeName><Initials>R</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-6171-7430</Identifier><AffiliationInfo><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.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Boussonnière</LastName><ForeName>Anne</ForeName><Initials>A</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-1113-099X</Identifier><AffiliationInfo><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.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Rouaud</LastName><ForeName>Jean-Christophe</ForeName><Initials>JC</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-4238-874X</Identifier><AffiliationInfo><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.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Lebreton</LastName><ForeName>Jacques</ForeName><Initials>J</Initials><Identifier Source="ORCID">http://orcid.org/0000-0003-2603-8982</Identifier><AffiliationInfo><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.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Graton</LastName><ForeName>Jérôme</ForeName><Initials>J</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-1114-200X</Identifier><AffiliationInfo><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.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Jacquemin</LastName><ForeName>Denis</ForeName><Initials>D</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-4217-0708</Identifier><AffiliationInfo><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.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Institut Universitaire de France, 1, rue Descartes, 75231, Paris Cedex 05, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Sebban</LastName><ForeName>Muriel</ForeName><Initials>M</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-7907-1092</Identifier><AffiliationInfo><Affiliation>Normandie Université, COBRA UMR6014, FR3038, Université de Rouen; INSA de Rouen; CNRS, 76821, Mont-Saint-Aignan Cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Oulyadi</LastName><ForeName>Hassan</ForeName><Initials>H</Initials><Identifier Source="ORCID">http://orcid.org/0000-0001-5813-1482</Identifier><AffiliationInfo><Affiliation>Normandie Université, COBRA UMR6014, FR3038, Université de Rouen; INSA de Rouen; CNRS, 76821, Mont-Saint-Aignan Cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hamdoun</LastName><ForeName>Ghanem</ForeName><Initials>G</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-1103-8499</Identifier><AffiliationInfo><Affiliation>Normandie Université, COBRA UMR6014, FR3038, Université de Rouen; INSA de Rouen; CNRS, 76821, Mont-Saint-Aignan Cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hancock</LastName><ForeName>Amber N</ForeName><Initials>AN</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-5269-7300</Identifier><AffiliationInfo><Affiliation>School of Chemistry and, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, 3010, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Schiesser</LastName><ForeName>Carl H</ForeName><Initials>CH</Initials><AffiliationInfo><Affiliation>School of Chemistry and, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, 3010, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Dénès</LastName><ForeName>Fabrice</ForeName><Initials>F</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-9791-3177</Identifier><AffiliationInfo><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.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>02</Month><Day>18</Day></ArticleDate></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>Chemistry</MedlineTA><NlmUniqueID>9513783</NlmUniqueID><ISSNLinking>0947-6539</ISSNLinking></MedlineJournalInfo><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">NMR spectroscopy</Keyword><Keyword MajorTopicYN="N">aluminium acetals</Keyword><Keyword MajorTopicYN="N">computational methods</Keyword><Keyword MajorTopicYN="N">radical cyclisation</Keyword><Keyword MajorTopicYN="N">reaction mechanisms</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2015</Year><Month>11</Month><Day>26</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>2</Month><Day>19</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>2</Month><Day>19</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2016</Year><Month>2</Month><Day>19</Day><Hour>6</Hour><Minute>1</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">26890896</ArticleId><ArticleId IdType="doi">10.1002/chem.201504780</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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