Photoinduzierte Cycloeliminierung konjugierter 5,6-Epoxy-triene der Jononreihe
UV-irradiation (λ = 254 nm; pentane) of the epoxy-triene 3 gives the isomers 4 (35 %), 5 (40 %) and 6 (5 %). The dihydrofurane 4 is the product of a thermal electrocyclization of the ylide a. On the other hand, a undergoes fragmentation to give the carbenoids b and c. Intramolecular addition of the...
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| Main Authors: | , , |
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
1978-12-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9425 |
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| _version_ | 1850170625172176896 |
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| author | A.P. Alder H.R. Wolf O. Jeger |
| author_facet | A.P. Alder H.R. Wolf O. Jeger |
| author_sort | A.P. Alder |
| collection | DOAJ |
| description |
UV-irradiation (λ = 254 nm; pentane) of the epoxy-triene 3 gives the isomers 4 (35 %), 5 (40 %) and 6 (5 %). The dihydrofurane 4 is the product of a thermal electrocyclization of the ylide a. On the other hand, a undergoes fragmentation to give the carbenoids b and c. Intramolecular addition of the carbene in b yields 6, whereas an analogous process in c gives 5. UV-irradiation (λ = 254 nm; pentane) of the epoxytriene 7 yields the isomers 8 (60%), 9 (25%) and 10 (ca. 5%). The tricyclic ketones 8 and 9 are products of an intermediate cyclopropene compound 11. 11 and the isomeric cyclopropene 10 are cyclization products of carbenoids (b' → 10; c' → 11) formed by fragmentation of an ylide a' (a' → b'; a' → c').
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| format | Article |
| id | doaj-art-795a8083afa64b98a3d30a410fa0d669 |
| institution | OA Journals |
| issn | 0009-4293 2673-2424 |
| language | deu |
| publishDate | 1978-12-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj-art-795a8083afa64b98a3d30a410fa0d6692025-08-20T02:20:26ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241978-12-01321210.2533/chimia.1978.464Photoinduzierte Cycloeliminierung konjugierter 5,6-Epoxy-triene der JononreiheA.P. Alder0H.R. Wolf1O. Jeger2Organisch-chemisches Laboratorium der Eidgenössischen Technischen Hochschule ZürichOrganisch-chemisches Laboratorium der Eidgenössischen Technischen Hochschule ZürichOrganisch-chemisches Laboratorium der Eidgenössischen Technischen Hochschule Zürich UV-irradiation (λ = 254 nm; pentane) of the epoxy-triene 3 gives the isomers 4 (35 %), 5 (40 %) and 6 (5 %). The dihydrofurane 4 is the product of a thermal electrocyclization of the ylide a. On the other hand, a undergoes fragmentation to give the carbenoids b and c. Intramolecular addition of the carbene in b yields 6, whereas an analogous process in c gives 5. UV-irradiation (λ = 254 nm; pentane) of the epoxytriene 7 yields the isomers 8 (60%), 9 (25%) and 10 (ca. 5%). The tricyclic ketones 8 and 9 are products of an intermediate cyclopropene compound 11. 11 and the isomeric cyclopropene 10 are cyclization products of carbenoids (b' → 10; c' → 11) formed by fragmentation of an ylide a' (a' → b'; a' → c'). https://www.chimia.ch/chimia/article/view/9425 |
| spellingShingle | A.P. Alder H.R. Wolf O. Jeger Photoinduzierte Cycloeliminierung konjugierter 5,6-Epoxy-triene der Jononreihe CHIMIA |
| title | Photoinduzierte Cycloeliminierung konjugierter 5,6-Epoxy-triene der Jononreihe |
| title_full | Photoinduzierte Cycloeliminierung konjugierter 5,6-Epoxy-triene der Jononreihe |
| title_fullStr | Photoinduzierte Cycloeliminierung konjugierter 5,6-Epoxy-triene der Jononreihe |
| title_full_unstemmed | Photoinduzierte Cycloeliminierung konjugierter 5,6-Epoxy-triene der Jononreihe |
| title_short | Photoinduzierte Cycloeliminierung konjugierter 5,6-Epoxy-triene der Jononreihe |
| title_sort | photoinduzierte cycloeliminierung konjugierter 5 6 epoxy triene der jononreihe |
| url | https://www.chimia.ch/chimia/article/view/9425 |
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