By Richard F. Heck
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Extra resources for Organotransition Metal Chemistry a Mechanistic Approach
Example text
Directions of addition often appear to be sterically controlled, but all the factors involved are not B. Methods of Preparation of Carbon-Transition Metal Bonds 37 well understood. Covalent additions generally occur with a preliminary coordination of the unsaturated compound, followed by a shift of the group adding from the metal to the coordinated, unsaturated compound. In coordinately saturated complexes, dissociation is usually the initial step of the reaction. c. 1:3 Additions Few 1:3 additions are known, but there is no reason why many reactions of this type with 1:3 dipolar compounds should not be possible.
Reactions of σ- and w-Bonded Derivatives 46 b. Carbon-Bonded Derivatives Two reaction courses are commonly observed with carbon σ-bonded transition metal complexes: (1) Ligand substitution by a reactant occurs and then the carbon group moves from metal to the ligand (covalent addition) or (2) an external reagent attacks the complex, either at the σ-bonded carbon group (SN2) or at the metal (oxidative addition). For example (34,94b, 94c), CH3COCo(CO)4 -co v [CH3COCo(CO)3] + co H5C2 C2HsC=CC2H5 C2H5 C=CC2H5 CH3COCo(CO)3 C2H5 > = < CH3C O -► products Co(CO)3 C6H5CH2COCo(CO)4 + C6H5NH2 -► QHsCHaCONHCeHs + HCo(CO)4 ci- PEt3 c.
Tetracarbonylmethylcobalt(I), for example, reacts with triphenylphosphine to form the acyl derivative (63). CH3 COCH3 P(C e H 5 ) 3 OC CO COCH3 P(C6H5)3 b. , olefins, carbonyl compounds, imines, and acetylenes, may occur by at least three mechanisms—ionic, radical, or covalent. 1. Ionic 1:2 Additions. The best known examples of this type of reaction occur with nontransition metal compounds. The addition of mercuric acetate to olefins in alcoholic solution is an example of a 1:2 ionic addition (64).