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Oxidative Ring Closure and Metal Triggered Ring Opening: Syntheses of Macrocyclic and Linear Hexapyrroles
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0001-6508-8355
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0002-1763-9383
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2014 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, no 24, 6354-6357 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2014. Vol. 16, no 24, 6354-6357 p.
Keyword [en]
Expanded Porphyrins, Coupled Oxidation, Solar-Cells, Tetraarylporphyrins, Phlorin, Bearing, Substituents, Molecule, Cleavage, Bilanes
National Category
Organic Chemistry
URN: urn:nbn:se:kth:diva-160768DOI: 10.1021/ol503132rISI: 000346759900023PubMedID: 25483884ScopusID: 2-s2.0-84919685142OAI: diva2:791643

QC 20150302

Available from: 2015-03-02 Created: 2015-02-27 Last updated: 2015-03-17Bibliographically approved

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Li, XinÅgren, Hans
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