Di-π-Methan-Umlagerungen von methylsubstituierten Allylbenzolen
Allylbenzene (3) and its derivatives bearing methyl groups at the aromatic ring or at C(1') of the allyl chain (see scheme 1-3, and 6) can cleanly be transformed into the corresponding cyclopropylbenzenes via a triplet di-π-methane rearrangement when irradiated with a mercury high pressure lam...
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
1981-01-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9504 |
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| _version_ | 1849310992890068992 |
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| author | Jean-Pierre Fasel Hans-Jürgen Hansen |
| author_facet | Jean-Pierre Fasel Hans-Jürgen Hansen |
| author_sort | Jean-Pierre Fasel |
| collection | DOAJ |
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Allylbenzene (3) and its derivatives bearing methyl groups at the aromatic ring or at C(1') of the allyl chain (see scheme 1-3, and 6) can cleanly be transformed into the corresponding cyclopropylbenzenes via a triplet di-π-methane rearrangement when irradiated with a mercury high pressure lamp through a filter of Jena glass in acetonitrile/acetone solution. Under the same conditions 2'-butenyl-3,5-dimethylbenzene (15) shows only a rapid trans,cis isomerization. Also no di-π-methane rearrangement is observed when (2'-methylallyl)-3,5-dimethylbenzene is irradiated in acetonitrile/acetone solution. Irradiations of the allylbenzenes in benzene solution using a quartz filter give as a rule complex reaction mixtures due to subsequent photoreactions of the primarily formed cyclopropylbenzenes (see scheme 4-6).
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| format | Article |
| id | doaj-art-b10dd0b5d65c43f2a477d22baf066517 |
| institution | Kabale University |
| issn | 0009-4293 2673-2424 |
| language | deu |
| publishDate | 1981-01-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj-art-b10dd0b5d65c43f2a477d22baf0665172025-08-20T03:53:33ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241981-01-0135110.2533/chimia.1981.9Di-π-Methan-Umlagerungen von methylsubstituierten AllylbenzolenJean-Pierre Fasel0Hans-Jürgen Hansen1Institut für Organische Chemie der Universität, Perolles, CH-1700 FreiburgInstitut für Organische Chemie der Universität, Perolles, CH-1700 Freiburg Allylbenzene (3) and its derivatives bearing methyl groups at the aromatic ring or at C(1') of the allyl chain (see scheme 1-3, and 6) can cleanly be transformed into the corresponding cyclopropylbenzenes via a triplet di-π-methane rearrangement when irradiated with a mercury high pressure lamp through a filter of Jena glass in acetonitrile/acetone solution. Under the same conditions 2'-butenyl-3,5-dimethylbenzene (15) shows only a rapid trans,cis isomerization. Also no di-π-methane rearrangement is observed when (2'-methylallyl)-3,5-dimethylbenzene is irradiated in acetonitrile/acetone solution. Irradiations of the allylbenzenes in benzene solution using a quartz filter give as a rule complex reaction mixtures due to subsequent photoreactions of the primarily formed cyclopropylbenzenes (see scheme 4-6). https://www.chimia.ch/chimia/article/view/9504 |
| spellingShingle | Jean-Pierre Fasel Hans-Jürgen Hansen Di-π-Methan-Umlagerungen von methylsubstituierten Allylbenzolen CHIMIA |
| title | Di-π-Methan-Umlagerungen von methylsubstituierten Allylbenzolen |
| title_full | Di-π-Methan-Umlagerungen von methylsubstituierten Allylbenzolen |
| title_fullStr | Di-π-Methan-Umlagerungen von methylsubstituierten Allylbenzolen |
| title_full_unstemmed | Di-π-Methan-Umlagerungen von methylsubstituierten Allylbenzolen |
| title_short | Di-π-Methan-Umlagerungen von methylsubstituierten Allylbenzolen |
| title_sort | di π methan umlagerungen von methylsubstituierten allylbenzolen |
| url | https://www.chimia.ch/chimia/article/view/9504 |
| work_keys_str_mv | AT jeanpierrefasel dipmethanumlagerungenvonmethylsubstituiertenallylbenzolen AT hansjurgenhansen dipmethanumlagerungenvonmethylsubstituiertenallylbenzolen |