Formation of an exceptionally stable ketene during phototransformations of bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophores
Photochemical reactions of bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophores like a 5,6 dibenzoyl moiety and bulky electron-deficient substituents like phenyl or isopropenyl at the bridgehead position were analyzed for the first time in different solvents and upon irradiation with different wa...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2020-09-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.16.190 |
| _version_ | 1818440828900605952 |
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| author | Asitanga Ghosh |
| author_facet | Asitanga Ghosh |
| author_sort | Asitanga Ghosh |
| collection | DOAJ |
| description | Photochemical reactions of bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophores like a 5,6 dibenzoyl moiety and bulky electron-deficient substituents like phenyl or isopropenyl at the bridgehead position were analyzed for the first time in different solvents and upon irradiation with different wavelengths. In all cases, a regioselective photoinduced 1,5-phenyl migration leading to vinyl ketenes from the more congested site of the molecule to the less congested one has been observed. The ketenes were exceptionally stable both in air and solution. Its stability studies in acetonitrile through time-dependent UV absorption spectra revealed that it remained almost unchanged at least for a couple of weeks. |
| first_indexed | 2024-12-14T18:18:34Z |
| format | Article |
| id | doaj.art-7bf7c8c1f87d4e19987ecf0a6768f293 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T18:18:34Z |
| publishDate | 2020-09-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-7bf7c8c1f87d4e19987ecf0a6768f2932022-12-21T22:52:07ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-09-011612297230310.3762/bjoc.16.1901860-5397-16-190Formation of an exceptionally stable ketene during phototransformations of bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophoresAsitanga Ghosh0Deptartment of Chemistry, Hooghly Mohsin College, Chinsurah, Hooghly, West Bengal, 712101, IndiaPhotochemical reactions of bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophores like a 5,6 dibenzoyl moiety and bulky electron-deficient substituents like phenyl or isopropenyl at the bridgehead position were analyzed for the first time in different solvents and upon irradiation with different wavelengths. In all cases, a regioselective photoinduced 1,5-phenyl migration leading to vinyl ketenes from the more congested site of the molecule to the less congested one has been observed. The ketenes were exceptionally stable both in air and solution. Its stability studies in acetonitrile through time-dependent UV absorption spectra revealed that it remained almost unchanged at least for a couple of weeks.https://doi.org/10.3762/bjoc.16.190α,β- and β,γ-enonesbridgehead positionketenemixed chromophores |
| spellingShingle | Asitanga Ghosh Formation of an exceptionally stable ketene during phototransformations of bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophores Beilstein Journal of Organic Chemistry α,β- and β,γ-enones bridgehead position ketene mixed chromophores |
| title | Formation of an exceptionally stable ketene during phototransformations of bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophores |
| title_full | Formation of an exceptionally stable ketene during phototransformations of bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophores |
| title_fullStr | Formation of an exceptionally stable ketene during phototransformations of bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophores |
| title_full_unstemmed | Formation of an exceptionally stable ketene during phototransformations of bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophores |
| title_short | Formation of an exceptionally stable ketene during phototransformations of bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophores |
| title_sort | formation of an exceptionally stable ketene during phototransformations of bicyclo 2 2 2 oct 5 en 2 ones having mixed chromophores |
| topic | α,β- and β,γ-enones bridgehead position ketene mixed chromophores |
| url | https://doi.org/10.3762/bjoc.16.190 |
| work_keys_str_mv | AT asitangaghosh formationofanexceptionallystableketeneduringphototransformationsofbicyclo222oct5en2oneshavingmixedchromophores |