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Reactions of Alkyl and Fluoroalkyl Radicals with Nickel, Iron, and Manganese Prophyrins
Guldi, Dirk M.,Kumar, Manmohan,Neta, P.,Hambright, Peter
, p. 9576 - 9581 (1992)
The reactions of alkyl (CH3, C2H5, n-C4H9, CH2CO2-, CH(CO2-)2, CH2CN) and fluoroalkyl (CF3, CF2Cl) radicals with nickel, iron, and manganese porphyrins (P) have been studied by radiolytic techniques in various solvents.All the radicals (R) react with FeIIP to form R-FeIIIP with a stable Fe-C bond.These products are oxidized by O2 to FeIIIP.Although NiIP and NiIIP also react rapidly with the radicals to form Ni-C bonds, only the reactions of fluoroalkyl radicals with NiIP yield stable products.Reactions of alkyl radicals with NiIP result in unstable R-NiIIP products (t1/2 several seconds) that eventually yield NiIIP.Reactions of alkyl radicals with NiIIP are reversible, and the short-lived R-NiIIIP products (t1/2 ca. milliseconds) disappear through radical reactions, with recovery of NiIIP.Alkyl radicals react rapidly with MnIIP, probably via addition to the metal, but the adduct gives MnIIIP immediately. .CF3 radicals also react with MnIIIP by addition to C=C bonds.
