CHED 867 |
Synthesis and Bergman cyclization of beta-extended porphyrenediynes
| John D. Spence and Domingo M. LLagostera. Department of Chemistry, Trinity University, One Trinity Place, San Antonio, TX 78212-7200 |
Condensation of a porphyrin 2,3-dione with 1,2-diamino arenediynes affords beta-extended porphyrenediynes. The incorporation of a quinoxaline spacer between the macrocycle and the enediyne unit prevents the meso-phenyl substituents from undergoing a tandem radical cyclization to the picenoporphyrin. Bergman cyclization of the acyclic porphyrenediyne 1 can be accomplished upon heating to 180 °C to produce the cyclic adduct 2. To improve the thermal activation and provide the opportunity to explore photochemical activation we are currently working to prepare the cyclic porphyrenediyne analog. The synthesis and Bergman cyclization of porphyrenediyne 1, its corresponding quinoxalenediyne model and our efforts towards cyclic analogs will be presented. |
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