Sauer, Jürgen and Breu, Josef and Holland, Uwe and Herges, Rainer and Neumann, Helfried and Kammermeier, Stefan (1997) Diels-Alder reactions of tetradehydrodianthracene with electron-deficient dienes. LIEBIGS ANNALEN-RECUEIL, 1997 (7). pp. 1473-1479. ISSN 0947-3440
Full text not available from this repository.Abstract
Theoretical calculations and simple MO considerations predict that a coplanar and spatially close arrangement of double bonds in structures such as tetradehydrodianthracene 1, should both lower the LUMO and raise the HOMO energy of the pi system. Thus the reactivity in Diels-Alder reactions towards electron-rich, as well as electron-deficient, dienes should be enhanced. The first effect has already been shown in a previous paper, the latter statement is now also confirmed by the reactivity of 1 in Diels-Alder reactions with inverse electron demand. In [4 + 2] cycloaddition reactions of 1 with 1,2,4,5-tetrazines 2 the electronic effect of 3,6 substituents in tetrazines is far outweighed by steric factors resulting in an unexpected reactivity sequence: 2a much greater than 2b approximate to 2e > 2d.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | C-C BOND; BI(ANTHRACENE-9,10-DIMETHYLENE) PHOTOISOMER; ENERGIES; MOLECULE; CRYSTAL; LENGTH; tetradehydrodianthracene; Diels-Alder reactions; cycloadditions; tetrazines; steric hindrance; kinetics; semiempirical calculations |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 25 Apr 2023 09:35 |
| Last Modified: | 25 Apr 2023 09:35 |
| URI: | https://pred.uni-regensburg.de/id/eprint/50724 |
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