Journal
ORGANIC LETTERS
Volume 16, Issue 24, Pages 6354-6357Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol503132r
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Funding
- NSFC/China [21472047, 91227201]
- Science Fund for Creative Research Groups [21421004]
- Oriental Scholarship
- Fundamental Research Funds for the Central Universities [WK1013002]
- [NCET-11-0638]
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A C6F5-substituted hexapyrrane (1) was synthesized in one step. Oxidative cyclization of 1 with DDQ afforded a phlorindipyrrin conjugate (2), and subsequent FeCl3-assisted oxidative cleavage of 2 afforded a terminally di-a-methoxy substituted hexapyrrin (3). On the other hand, oxidation of 1 with FeCl3 afforded 3, a hexapyrrinone Fe3+ complex (4), and a hexaphyrin (1,1,1,1,1,0) (5). These results indicate that the oxidation of hexapyrranes may be developed as an effective approach for the syntheses of novel linear and macrocyclic hexapyrroles.
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