4-ATOM-LINKED CAPPED PORPHYRINS - SYNTHESIS AND CHARACTERIZATION

Citation
Mr. Johnson et al., 4-ATOM-LINKED CAPPED PORPHYRINS - SYNTHESIS AND CHARACTERIZATION, Journal of organic chemistry, 61(10), 1996, pp. 3298-3303
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
61
Issue
10
Year of publication
1996
Pages
3298 - 3303
Database
ISI
SICI code
0022-3263(1996)61:10<3298:4CP-SA>2.0.ZU;2-4
Abstract
Three new capped porphyrins, H-2(OC(2)OPor) (7), H-2(OC(CO)NPor) (13), and H-2(OC(2)NPor) (14), to be used as heme model compounds, have bee n synthesized and characterized. These compounds have the shortest lin kages between cap and porphyrin plane of any four-arm capped porphyrin s synthesized to date. The general synthetic procedure for H-2(OC(2)OP or) involves the reaction of a tetraaldehyde ''cap'' with pyrrole to f orm the capped porphyrin. In the synthesis of the tetraamide-capped po rphyrin, H-2(OC(CO)NPor), a tetraacid chloride cap is reacted with ,al pha,alpha,alpha-tetra-(o-aminophenyl)porphyrin. The amide groups may b e reduced to form H-2(OC(2)NPor). With the use of FeBr2, Fe2+ may be i nserted in high yield into Ha(2)(OC(2)OPor) and H-2(OC(CO)NPor). The c rystal structures of H-2(OC(2)NPor), Fe(OC(2)OPor)(OMe), and [Fe(OC(2) OPor)](2)(mu-O) provide details on the types and amounts of cap expans ion necessary to accommodate small ligands of biological interest, suc h as O-2 and CO.