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Arene complexes of transition metals in reactions with nucleophilic reagents. XVIII. Effect of substituents in chlorobenzene derivatives coordinated with the Cr(CO)/sub 3/ fragment on substitution rate of the chlorine atom by action of sodium methoxide in methanol

Journal Article · · J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:6008648
The effect of the substituents X in complexes of the (XC/sub 6/H/sub 4/Cl)Cr(CO)/sub 3/ type on the rate of nucleophilic substitution of the chlorine atom by the action of sodium methoxide in methanol at 40-70/degree/C corresponds to the series p-OCH/sub 3/ < 0-CH/sub 3/ < p-CH/sub 3/ < m-CH/sub 3/ < H < m-OCH/sub 3/ < p-Cl < o-Cl < m-CO/sub 2/CH/sub 3/ < m-Cl < p-CO/sub 2/CH/sub 3/ and is described in the case of meta and para substituents by the correlation equation log k/sub 70/degree/C/ = 3.56/sigma/ - 3.95. It was concluded that the nature of the effect of substituents on the rate of aromatic nucleophilic substitution in the arene complexes of transition metals depends on the charge of the intermediate.
Research Organization:
Novosibirsk Institute of Organic Chemistry (USSR)
OSTI ID:
6008648
Journal Information:
J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:5; ISSN JOCYA
Country of Publication:
United States
Language:
English