The Cope Rearrangement - a Reaction with a Manifold Mechanism?
For the Cope rearrangement of hexa-1,5-dienes (cf. 1) to isomeric forms (cf. 1'), more mechanisms are at one’s disposal than was hitherto accepted. Depending on the choise of the structure, the kind of substituents of the Cope system or on the reaction conditions, most of the thinkable mechani...
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
1976-09-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9321 |
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| author | Rudolf Wehrli Daniel Belluš Hans-Jürgen Hansen Hans Schmid |
| author_facet | Rudolf Wehrli Daniel Belluš Hans-Jürgen Hansen Hans Schmid |
| author_sort | Rudolf Wehrli |
| collection | DOAJ |
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For the Cope rearrangement of hexa-1,5-dienes (cf. 1) to isomeric forms (cf. 1'), more mechanisms are at one’s disposal than was hitherto accepted. Depending on the choise of the structure, the kind of substituents of the Cope system or on the reaction conditions, most of the thinkable mechanisms can be defined. Twostep Cope processes are characterized by dissociation and recombination or by the intervention of diradicals or zwitterions as intermediates. Concerted processes can occur via the “classical” pericyclic (aromatic) or via a diradicaloid transition state. Whereas the unsubstituted hexa-1,5-diene and its derivatives with conjugative substituents in positions 1,3,4 or 6 follow the pericyclic route, systems with radical stabilizing substituents in positions 2,5 prefer to react via the diradicaloid pathway. Thus, hexa-1,5-dienes represent, from a mechanistical standpoint, quite ductile systems.
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| format | Article |
| id | doaj-art-9f4d3fa6263f4bf39d866d6784972082 |
| institution | OA Journals |
| issn | 0009-4293 2673-2424 |
| language | deu |
| publishDate | 1976-09-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj-art-9f4d3fa6263f4bf39d866d67849720822025-08-20T01:47:42ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241976-09-0130910.2533/chimia.1976.416The Cope Rearrangement - a Reaction with a Manifold Mechanism?Rudolf Wehrli0Daniel Belluš1Hans-Jürgen Hansen2Hans Schmid3Organisch-chemisches Institut der Universität Zürich, Rämistrasse 76, CH-8001 ZürichZentrale Forschungslaboratorien, Ciba- Geigy AG, CH-4002 BaselInstitut de chimie organique de l’Université de Fribourg, Pérolles, CH-1700 FribourgOrganisch-chemisches Institut der Universität Zürich, Rämistrasse 76, CH-8001 Zürich For the Cope rearrangement of hexa-1,5-dienes (cf. 1) to isomeric forms (cf. 1'), more mechanisms are at one’s disposal than was hitherto accepted. Depending on the choise of the structure, the kind of substituents of the Cope system or on the reaction conditions, most of the thinkable mechanisms can be defined. Twostep Cope processes are characterized by dissociation and recombination or by the intervention of diradicals or zwitterions as intermediates. Concerted processes can occur via the “classical” pericyclic (aromatic) or via a diradicaloid transition state. Whereas the unsubstituted hexa-1,5-diene and its derivatives with conjugative substituents in positions 1,3,4 or 6 follow the pericyclic route, systems with radical stabilizing substituents in positions 2,5 prefer to react via the diradicaloid pathway. Thus, hexa-1,5-dienes represent, from a mechanistical standpoint, quite ductile systems. https://www.chimia.ch/chimia/article/view/9321 |
| spellingShingle | Rudolf Wehrli Daniel Belluš Hans-Jürgen Hansen Hans Schmid The Cope Rearrangement - a Reaction with a Manifold Mechanism? CHIMIA |
| title | The Cope Rearrangement - a Reaction with a Manifold Mechanism? |
| title_full | The Cope Rearrangement - a Reaction with a Manifold Mechanism? |
| title_fullStr | The Cope Rearrangement - a Reaction with a Manifold Mechanism? |
| title_full_unstemmed | The Cope Rearrangement - a Reaction with a Manifold Mechanism? |
| title_short | The Cope Rearrangement - a Reaction with a Manifold Mechanism? |
| title_sort | cope rearrangement a reaction with a manifold mechanism |
| url | https://www.chimia.ch/chimia/article/view/9321 |
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