title: Oxidative ring closure and metal triggered ring opening: syntheses of macrocyclic and linear hexapyrroles.
abstract: A C6F5-substituted hexapyrrane (1) was synthesized in one step. Oxidative cyclization of 1 with DDQ afforded a phlorin-dipyrrin conjugate (2), and subsequent FeCl3-assisted oxidative cleavage of 2 afforded a terminally di-α-methoxy substituted hexapyrrin (3). On the other hand, oxidation of 1 with FeCl3 afforded 3, a hexapyrrinone Fe(3+) 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.
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology , Shanghai 200237, P. R. China.
authors.forename: Kai
authors.initials: K
authors.lastname: Zhang
authors.forename: Pingchun
authors.initials: P
authors.lastname: Wei
authors.forename: Xin
authors.initials: X
authors.lastname: Li
authors.forename: Hans
authors.initials: H
authors.lastname: Ågren
authors.forename: Yongshu
authors.initials: Y
authors.lastname: Xie
mesh_terms: D002384:Catalysis; D056831:Coordination Complexes / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D056831:Coordination Complexes; D047028:Macrocyclic Compounds; D011758:Pyrroles