Sauer, Juergen and Baeuerlein, Peter and Ebenbeck, Wolfgang and Dyllick-Brenzinger, Rainer and Gousetis, Charalampos and Sichert, Heinz and Troll, Theodor and Wallfahrer, Uwe (2001) The cycloaddition-cycloelimination pathway to homotropilidenes - Synthesis and properties of homotropilidenes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (14). pp. 2639-2657. ISSN 1434-193X
Full text not available from this repository. (Request a copy)Abstract
The cycloaddition-cycloelimination reaction sequence between 3,6-disubstituted 1,2,4,5-tetrazines 9 and various cyclopropenes 10 provides 3,4-diazanorcaradienes 11, which undergo [4+2] cycloadditions with additional cyclopropenes 10 to form tetracyclic azo compounds 12. Photolysis of these compounds, with accompanying loss of nitrogen, affords homotropilidenes (bicyclo[5.1.0]octa-2,5-dienes) 13-26. Substituents at various positions of the homotropilidene skeleton have been observed to exert significant influences on the Cope rearrangement rate and, in cases of unsymmetrically substituted homotropilidenes, on the equilibrium positions.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | COPE REARRANGEMENT; AZOALKANES; SPECTROSCOPY; MOLECULES; STATE; azo compounds; cycloadditions; kinetics; photolysis; rearrangements; substituent effects |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 11 Jan 2022 06:44 |
| Last Modified: | 11 Jan 2022 06:44 |
| URI: | https://pred.uni-regensburg.de/id/eprint/41283 |
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