Valence isomers of Aromatic Compounds: On the Mechanism of the Katz Reaction
Lithium salts of small and medium-sized aromatic anions react with methylene chloride and alkyllithium to afford bridged bicyclobutanes or related polycyclic compounds. We demonstrate that the three new carbon-carbon bonds formed in the course of these title reactions result from a tandem of carben...
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| Main Authors: | , , |
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
1987-02-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9770 |
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| _version_ | 1850283592053161984 |
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| author | Ulrich Burger Pierre Jean Thorel Yves Mentha |
| author_facet | Ulrich Burger Pierre Jean Thorel Yves Mentha |
| author_sort | Ulrich Burger |
| collection | DOAJ |
| description |
Lithium salts of small and medium-sized aromatic anions react with methylene chloride and alkyllithium to afford bridged bicyclobutanes or related polycyclic compounds. We demonstrate that the three new carbon-carbon bonds formed in the course of these title reactions result from a tandem of carbenoid processes. Formation of exocyclic carbenoids precedes intramolecular cheletropic addition and ring enlargement. Neither H-migration nor CH-insertion is observed throughout these processes. Key intermediates have been generated by independent routes.
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| format | Article |
| id | doaj-art-8e7cd587162b4bb680beff670b542960 |
| institution | OA Journals |
| issn | 0009-4293 2673-2424 |
| language | deu |
| publishDate | 1987-02-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj-art-8e7cd587162b4bb680beff670b5429602025-08-20T01:47:45ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241987-02-01411-210.2533/chimia.1987.26Valence isomers of Aromatic Compounds: On the Mechanism of the Katz ReactionUlrich Burger0Pierre Jean Thorel1Yves Mentha2Département de Chimie Organique Université de Genève 30, quai Ernest-Ansermet, CH-1211 Genève 4Département de Chimie Organique, Université de Genève, 30, quai Ernest-Ansermet, CH-1211 Genève 4Département de Chimie Organique Université de Genève 30, quai Ernest-Ansermet, CH-1211 Genève 4 Lithium salts of small and medium-sized aromatic anions react with methylene chloride and alkyllithium to afford bridged bicyclobutanes or related polycyclic compounds. We demonstrate that the three new carbon-carbon bonds formed in the course of these title reactions result from a tandem of carbenoid processes. Formation of exocyclic carbenoids precedes intramolecular cheletropic addition and ring enlargement. Neither H-migration nor CH-insertion is observed throughout these processes. Key intermediates have been generated by independent routes. https://www.chimia.ch/chimia/article/view/9770 |
| spellingShingle | Ulrich Burger Pierre Jean Thorel Yves Mentha Valence isomers of Aromatic Compounds: On the Mechanism of the Katz Reaction CHIMIA |
| title | Valence isomers of Aromatic Compounds: On the Mechanism of the Katz Reaction |
| title_full | Valence isomers of Aromatic Compounds: On the Mechanism of the Katz Reaction |
| title_fullStr | Valence isomers of Aromatic Compounds: On the Mechanism of the Katz Reaction |
| title_full_unstemmed | Valence isomers of Aromatic Compounds: On the Mechanism of the Katz Reaction |
| title_short | Valence isomers of Aromatic Compounds: On the Mechanism of the Katz Reaction |
| title_sort | valence isomers of aromatic compounds on the mechanism of the katz reaction |
| url | https://www.chimia.ch/chimia/article/view/9770 |
| work_keys_str_mv | AT ulrichburger valenceisomersofaromaticcompoundsonthemechanismofthekatzreaction AT pierrejeanthorel valenceisomersofaromaticcompoundsonthemechanismofthekatzreaction AT yvesmentha valenceisomersofaromaticcompoundsonthemechanismofthekatzreaction |