Journal of the Chemical Society, Dalton Transactions p. 1504 - 1514 (1981)
Update date:2022-08-05
Topics:
Nishinaga, Akira
Tomita, Haruo
Nishizawa, Kanji
Matsuura, Teruo
Ooi, Shunichiro
Hirotsu, Ken
The oxygenation of 2,6-di-t-butylphenols with five-co-ordinated cobalt(II) Schiff-base complexes in aprotic solvents, such as CH2Cl2, thf, and dmf (thf = tetrahydrofuran, dmf = dimethylformamide), has been found to result in regioselective formation of peroxyquinolatocobalt(III) complexes.The regioselectivity depends on the nature of the substituent at the 4-position of the phenol used: 4-alkyl-2,6-di-t-butylphenols(1) afford peroxy-p-quinolatocobalt(III) complexes, whereas peroxy-o-quinolato-complexes are formed from 4-aryl-2,6-di-t-butyl-phenols (4).The initiation of the oxygenation is hydrogen abstraction by superoxocobalt(III) species from the phenols to give the corresponding phenoxy-radicals (10).Rapid reduction of (10) with cobalt(II) species follows giving rise to a phenolatocobalt(III) complex intermediate, within which dioxygen is incorporated.The regioselectivity of the oxygenation is attributable to the formation of the phenolatocobalt(III) complex intermediate.Crystals of the peroxy-p-quinolatocobalt(III) complex (2a) are orthorombic, space group P212121, with a = 33.749(11), b = 11.844(5), c = 9.329(4) Angstroem, and Z = 4.The crystal structure has been refined from 3 018 diffractometer data to R = 0.067.
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Doi:10.1021/ol0483549
(2004)Doi:10.1021/jm00143a019
(1981)Doi:10.1021/jo00215a015
(1985)Doi:10.1007/BF00899678
(1981)Doi:10.1246/bcsj.54.2225
(1981)Doi:10.1016/S0040-4039(01)92904-1
(1981)
