UNUSUAL BASE-INDUCED REARRANGEMENT OF EXO-9-OXABICYCLO[4.2.1]NON-7-ENE OXIDE TO EXO-8-HYDROXYBICYCLO[3.3.0]OCTAN-2-ONE
Reaction of exo-9-oxabicyclo[4.2.1]non-7-ene oxide with n-BuLi gives exo-8-hydroxybicyclo[3.3.0]octan-2-one. Potential reaction pathways for this unusual rearrangement were evaluated with the aid of computational studies. The process is proposed to proceed by elimination to a transient allene oxide,...
| Main Authors: | , , , |
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| Format: | Journal article |
| Language: | English |
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2012
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| _version_ | 1797098791039401984 |
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| author | Hodgson, D Stent, M Paton, R Wilson, F |
| author_facet | Hodgson, D Stent, M Paton, R Wilson, F |
| author_sort | Hodgson, D |
| collection | OXFORD |
| description | Reaction of exo-9-oxabicyclo[4.2.1]non-7-ene oxide with n-BuLi gives exo-8-hydroxybicyclo[3.3.0]octan-2-one. Potential reaction pathways for this unusual rearrangement were evaluated with the aid of computational studies. The process is proposed to proceed by elimination to a transient allene oxide, which rearranges to a trans-epoxide enolate before undergoing epoxide α-lithiation and transannular C-H insertion. © 2012 The Japan Institute of Heterocyclic Chemistry. |
| first_indexed | 2024-03-07T05:14:42Z |
| format | Journal article |
| id | oxford-uuid:dcca5eaf-c6f1-4ec5-963f-f974d8e6ed6a |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:14:42Z |
| publishDate | 2012 |
| record_format | dspace |
| spelling | oxford-uuid:dcca5eaf-c6f1-4ec5-963f-f974d8e6ed6a2022-03-27T09:20:02ZUNUSUAL BASE-INDUCED REARRANGEMENT OF EXO-9-OXABICYCLO[4.2.1]NON-7-ENE OXIDE TO EXO-8-HYDROXYBICYCLO[3.3.0]OCTAN-2-ONEJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:dcca5eaf-c6f1-4ec5-963f-f974d8e6ed6aEnglishSymplectic Elements at Oxford2012Hodgson, DStent, MPaton, RWilson, FReaction of exo-9-oxabicyclo[4.2.1]non-7-ene oxide with n-BuLi gives exo-8-hydroxybicyclo[3.3.0]octan-2-one. Potential reaction pathways for this unusual rearrangement were evaluated with the aid of computational studies. The process is proposed to proceed by elimination to a transient allene oxide, which rearranges to a trans-epoxide enolate before undergoing epoxide α-lithiation and transannular C-H insertion. © 2012 The Japan Institute of Heterocyclic Chemistry. |
| spellingShingle | Hodgson, D Stent, M Paton, R Wilson, F UNUSUAL BASE-INDUCED REARRANGEMENT OF EXO-9-OXABICYCLO[4.2.1]NON-7-ENE OXIDE TO EXO-8-HYDROXYBICYCLO[3.3.0]OCTAN-2-ONE |
| title | UNUSUAL BASE-INDUCED REARRANGEMENT OF EXO-9-OXABICYCLO[4.2.1]NON-7-ENE OXIDE TO EXO-8-HYDROXYBICYCLO[3.3.0]OCTAN-2-ONE |
| title_full | UNUSUAL BASE-INDUCED REARRANGEMENT OF EXO-9-OXABICYCLO[4.2.1]NON-7-ENE OXIDE TO EXO-8-HYDROXYBICYCLO[3.3.0]OCTAN-2-ONE |
| title_fullStr | UNUSUAL BASE-INDUCED REARRANGEMENT OF EXO-9-OXABICYCLO[4.2.1]NON-7-ENE OXIDE TO EXO-8-HYDROXYBICYCLO[3.3.0]OCTAN-2-ONE |
| title_full_unstemmed | UNUSUAL BASE-INDUCED REARRANGEMENT OF EXO-9-OXABICYCLO[4.2.1]NON-7-ENE OXIDE TO EXO-8-HYDROXYBICYCLO[3.3.0]OCTAN-2-ONE |
| title_short | UNUSUAL BASE-INDUCED REARRANGEMENT OF EXO-9-OXABICYCLO[4.2.1]NON-7-ENE OXIDE TO EXO-8-HYDROXYBICYCLO[3.3.0]OCTAN-2-ONE |
| title_sort | unusual base induced rearrangement of exo 9 oxabicyclo 4 2 1 non 7 ene oxide to exo 8 hydroxybicyclo 3 3 0 octan 2 one |
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