Klein, Michael and Walenzyk, Thomas and Koenig, Burkhard (2004) Electronic effects on the Bergman cyclisation of enediynes. A review. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 69 (5). pp. 945-965. ISSN 0010-0765
Full text not available from this repository. (Request a copy)Abstract
The thermal cyclisation of enediynes to benzene-1,4-diyl diradicals (Bergman cyclisation) is affected by geometrical and electronic conditions. While the effect of ring strain or conformational constrains on the cyclisation temperature has been investigated in detail, electronic contributions have been less studied. Often geometrical and electronic contributions cannot be clearly distinguished. In most cases metal ion chelation does involve both. In this review we have summarised clear-cut observations of electronic substituents effects on the thermal enediyne reactivity. The effects of substituents in the vinylic and terminal alkyne position, the influence of benzo-fusion and hetarene fusion, as well as the changes induced by heteroatoms in the enediyne skeleton, are within the scope of this review. With the exception of more complex heterocyclic hetarene-fused enediynes the experimental data of electronic substituent effects on the thermal Bergman cyclisation of enediynes follow theoretical predictions. A review with 57 references.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | POTENT ANTITUMOR ANTIBIOTICS; THERMAL REACTIVITY; AMBIENT-TEMPERATURE; MONOCYCLIC ENEDIYNE; BIRADICAL FORMATION; ENYNE-ALLENES; PARA-BENZYNE; DYNEMICIN-A; AZA-BERGMAN; CYCLOAROMATIZATION; enediynes; Bergman cyclisations; electronic substituent effects; alkynes; DNA; cleavage agents; antibiotics; cytotoxic compounds |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Petra Gürster |
| Date Deposited: | 20 Jul 2021 09:57 |
| Last Modified: | 20 Jul 2021 09:57 |
| URI: | https://pred.uni-regensburg.de/id/eprint/38135 |
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