The oxidative addition of the carbon-hydrogen bond is not the rate-determining step in the remote functionalization of nitriles by bare iron(I) ions

1989 ◽  
Vol 111 (13) ◽  
pp. 4561-4563 ◽  
Author(s):  
Gregor Czekay ◽  
Thomas Drewello ◽  
Helmut Schwarz
2020 ◽  
Vol 929 ◽  
pp. 121571
Author(s):  
Alexander F. Schmidt ◽  
Anna A. Kurokhtina ◽  
Elizaveta V. Larina ◽  
Elena V. Vidyaeva ◽  
Nadezhda A. Lagoda

1986 ◽  
Vol 64 (5) ◽  
pp. 897-903 ◽  
Author(s):  
Brian R. James ◽  
Robert H. Morris ◽  
Pal Kvintovics

Synthetic routes to hydridoiridium(III) dimethylsulfoxide complexes via oxidative addition of HCl or H2 to precursor insitu iridium(I) species are described. The complexes, trans, mer-IrHCl2(DMSO)3 (1a) and cis, mer-IrH2Cl(DMSO)3 (2), have been characterized by 1H nmr and ir, and contain only S-bonded sulphoxide, DMSO. Comparison is made with data for other isomers reported in the literature, and some discrepancies are discussed. The decomposition of 1a and 2 in chloroform leads to isomers of IrCl3(DMSO)3, while (2) with HCl generates cis,cis IrHCl2(DMSO)2(DMSO) with the O-bonded sulfoxide trans to hydride. The reaction of 1a in dichloromethane with dioxygen occurs with a 1:1 stoichiometry and generates two complexes tentatively formulated as Ir(OH)Cl2(DMSO)2H2O (3) and IrCl2(O2)(DMSO)2DMSO (4); a hydroperoxide intermediate (Ir—OOH) initially formed from 1a is considered to react with further 1a in the rate-determining step. Oxidation of coordinated DMSO to the sulphone is not observed, implying that such a catalyzed O2-oxidation reported earlier in aqueous 2-propanol proceeds via reaction of IrOOH with free DMSO, or else via free hydrogen peroxide.


1975 ◽  
Vol 53 (6) ◽  
pp. 845-854 ◽  
Author(s):  
Herbert L. Holland ◽  
Barbara J. Auret

The mechanism of the C-21 hydroxylation of progesterone (1a) by Aspergillusniger ATCC 9142 to give 11-deoxycorticosterone (1b) has been studied by the use of progesterone derivatives and of C-21 deuterium labelled progesterones. The requirement of the C-21 hydroxylase system for a C-20 carbonyl group is demonstrated and the possibility of the involvement of this group, in the C-20,21 enol form, in the C-21 hydroxylation reaction has been discussed. However, on the basis of the observed deuterium isotope effect (KH/KD = 1.25), a mechanism for the microbial C-21 hydroxylation reaction is proposed in which the rate-determining step is the direct insertion of oxygen into a C-21 carbon–hydrogen bond and not one involving enolization of the C-20 carbonyl.In addition, C-11α and C-15β hydroxylation of both 20α- and 20β-hydroxypregn-4-ene-3-one (2a and 2b) by A. niger has been observed.


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