Synthese von neuen Heptalenderivaten
Guaiazulene (9), in boiling 1,2,3,4-tetrahydronaphthalene, reacts with dimethyl acetylenedicarboxylate (ADM) to yield dimethyl-7-isopropyl-5,10-dimethylheptalene-1,2-dicarboxylate (10) as the main product and dimethyl-7-isopropyl-4-methylazulene-1,2-dicarboxylate (11) as a by-product (see scheme 2)...
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| Main Authors: | , , |
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
1979-09-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9451 |
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| _version_ | 1850283704565366784 |
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| author | Werner Bernhard Hans-Rudolf Zumbrunnen Hans-Jürgen Hansen |
| author_facet | Werner Bernhard Hans-Rudolf Zumbrunnen Hans-Jürgen Hansen |
| author_sort | Werner Bernhard |
| collection | DOAJ |
| description |
Guaiazulene (9), in boiling 1,2,3,4-tetrahydronaphthalene, reacts with dimethyl acetylenedicarboxylate (ADM) to yield dimethyl-7-isopropyl-5,10-dimethylheptalene-1,2-dicarboxylate (10) as the main product and dimethyl-7-isopropyl-4-methylazulene-1,2-dicarboxylate (11) as a by-product (see scheme 2). A second heptalene derivative, occurring only in minor amounts in the reaction mixture, was found to be formed from 10 in a consecutive thermal reaction (scheme 2). Its structure, namely dimethyl-7-isopropyl- 5,10-dimethylheptalene-1,3-dicarboxylate (13), was established by spectroscopic means (for cyclic voltametry of the new compounds see figure and table). Both heptalene derivative 10 and 13, as well as the heptalene compound formed in the reaction of ADM with vetivazulene (see footnote 2), exhibit in 1H- and 13 C-NMR-spectroscopy isopropyl moieties with diastereotopic methyl groups, i.e. the chiral heptalene structure does not invert according to the NMR time scale.
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| format | Article |
| id | doaj-art-cc4c9f47238641038188d57bb433ade3 |
| institution | OA Journals |
| issn | 0009-4293 2673-2424 |
| language | deu |
| publishDate | 1979-09-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj-art-cc4c9f47238641038188d57bb433ade32025-08-20T01:47:44ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241979-09-0133910.2533/chimia.1979.324Synthese von neuen HeptalenderivatenWerner Bernhard0Hans-Rudolf Zumbrunnen1Hans-Jürgen Hansen2Institut für Organische Chemie der Universität Freiburg i. Ü.Institut für Anrganische Chemie der Universität Freiburg i. Ü.Institut für Organische Chemie der Universität Freiburg i. Ü. Guaiazulene (9), in boiling 1,2,3,4-tetrahydronaphthalene, reacts with dimethyl acetylenedicarboxylate (ADM) to yield dimethyl-7-isopropyl-5,10-dimethylheptalene-1,2-dicarboxylate (10) as the main product and dimethyl-7-isopropyl-4-methylazulene-1,2-dicarboxylate (11) as a by-product (see scheme 2). A second heptalene derivative, occurring only in minor amounts in the reaction mixture, was found to be formed from 10 in a consecutive thermal reaction (scheme 2). Its structure, namely dimethyl-7-isopropyl- 5,10-dimethylheptalene-1,3-dicarboxylate (13), was established by spectroscopic means (for cyclic voltametry of the new compounds see figure and table). Both heptalene derivative 10 and 13, as well as the heptalene compound formed in the reaction of ADM with vetivazulene (see footnote 2), exhibit in 1H- and 13 C-NMR-spectroscopy isopropyl moieties with diastereotopic methyl groups, i.e. the chiral heptalene structure does not invert according to the NMR time scale. https://www.chimia.ch/chimia/article/view/9451 |
| spellingShingle | Werner Bernhard Hans-Rudolf Zumbrunnen Hans-Jürgen Hansen Synthese von neuen Heptalenderivaten CHIMIA |
| title | Synthese von neuen Heptalenderivaten |
| title_full | Synthese von neuen Heptalenderivaten |
| title_fullStr | Synthese von neuen Heptalenderivaten |
| title_full_unstemmed | Synthese von neuen Heptalenderivaten |
| title_short | Synthese von neuen Heptalenderivaten |
| title_sort | synthese von neuen heptalenderivaten |
| url | https://www.chimia.ch/chimia/article/view/9451 |
| work_keys_str_mv | AT wernerbernhard synthesevonneuenheptalenderivaten AT hansrudolfzumbrunnen synthesevonneuenheptalenderivaten AT hansjurgenhansen synthesevonneuenheptalenderivaten |