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Skeletal Rearrangement of Twisted Thia‐Norhexaphyrin: Multiply Annulated Polypyrrolic Aromatic Macrocycles.
- Source :
-
Angewandte Chemie . 4/23/2019, Vol. 131 Issue 18, p5986-5990. 5p. - Publication Year :
- 2019
-
Abstract
- A hybrid thia‐norhexaphyrin comprising a directly linked N‐confused pyrrole and thiophene unit (1) revealed unique macrocycle transformations to afford multiply inner‐annulated aromatic macrocycles. Oxidation with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone triggered a cleavage of the C−S bond of the thiophene unit, accompanied with skeletal rearrangement to afford unique π‐conjugated products: a thiopyrrolo‐pentaphyrin embedded with a pyrrolo[1,2]isothiazole (2), a sulfur‐free pentaphyrin incorporating an indolizine moiety (3), and a thiopyranyltriphyrinoid containing a 2H‐thiopyran unit (4). Furthermore, 2 underwent desulfurization reactions to afford a fused pentaphyrin containing a pyrrolizine moiety (5) under mild conditions. Using expanded porphyrin scaffolds, oxidative thiophene cleavage and desulfurization of the hitherto unknown N‐confused core‐modified macrocycles would be a practical approach for developing unique polypyrrolic aromatic macrocycles. [ABSTRACT FROM AUTHOR]
- Subjects :
- *MACROCYCLIC compounds
*PYRROLES
*THIOPHENES
*TISSUE scaffolds
*DESULFURIZATION
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 131
- Issue :
- 18
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 135862217
- Full Text :
- https://doi.org/10.1002/ange.201900010