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Chem. Soc. 67, 2003 (1945). : Angew. Chem. 81, 150 (1969). : Angew. Chem. 83, 239 (1971). Barraclough, C. , Martin, R. , Stewart, I. : Austr. J. Chem. 22, 891 (1969). Witte, E. : Dissertation Univ. Tiibingen. 37 G. H~ifelinger 87) as) 89) 90) 91) 92) 93) 94) 9s) 96) 97) 98) 99) 100) 1Ol) 1o2) 10a) 1o4) 10s) lO6) lO7) lO8) lO9) 110) 111) 112) 113) 114) 115) 116) 117) 118) 119) 12o) 121) 122) 123) 124) 125) 38 Lennard-Jones, J. : Trans. Faraday Soc. 25, 668 (1929). Mulliken, R. : J. Chem. Phys. 3, 375 (1935).

1 , Ph-C-Fe(CO)n_ t I01 > P h - C - P h ao) ; A further example of this type o f reaction was shown by Tsutsumi and Yoshisato in furane formation, a-Bromoketones react with Ni(CO)4 ; the products of the reaction are different depending on the solvent used in the reaction. Thus, in tetrahydrofurane, diketone is obtained. On the other hand, furane derivatives are obtained in dimethylformamide. As an intermediate of the furane formation, an e p o x y c o m p o u n d was isolated. THF R - C - C H - B r + Ni(CO), [DMF R R' I I R-C-CH-CH-COR 101 R' 0 R R R' The reaction can be explained by oxidative addition of the carbon-bromine bond to form a nickel-carbon bond, followed by a nucleophilic attack o f the nickel-carbon bond on the carbonyl of the other bromoketone.

In the presence of certain ligands (carbon monoxide, CN, pyridine, bipyridine, triaryl, or trailkylphosphine), this reaction in some instances leads to stable isolable o-bonded alkyl transition 56 Organic Synthesis by Means of Transition Metal Complexes metal complexes. One example is the reaction of iron acetylacetonate with triethylaluminum in the presence of bipyridine to form a diethyliron complex 6s-7~). jN Wilkinson and coworkers obtained stable alkyl complexes by the reaction of transition metal halides or complex halides with trimethylsilylmethyl lithium 7~).

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