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- Title
Skeletal Rearrangement of Twisted Thia‐Norhexaphyrin: Multiply Annulated Polypyrrolic Aromatic Macrocycles.
- Authors
Li, Qizhao; Ishida, Masatoshi; Kai, Hiroto; Gu, Tingting; Li, Chengjie; Li, Xin; Baryshnikov, Glib; Liang, Xu; Zhu, Weihua; Ågren, Hans; Furuta, Hiroyuki; Xie, Yongshu
- 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.
- Subjects
MACROCYCLIC compounds; PYRROLES; THIOPHENES; TISSUE scaffolds; DESULFURIZATION
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 18, p5986
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201900010