By D. Bethell (ed.)
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Extra resources for Advances in Physical Organic Chemistry, Vol. 23
This species reacts with methyl iodide to give the binuclear product shown in (23). However, it is difficult to investigate the stereochemistry of this simple reaction because reactions with alkyl halides involving alkyl groups larger than ethyl d o not lead to stable products. The stereochemistry of the metallacycle formation was determined as shown in (24). The alkylation of the dicobalt anion with a,y-diiodides occurs with a complicated stereochemistry as evidenced by the studies with mesoand (f)-2,4-dimethylpentane.
In this catalytic cycle, the cis-[RhH(CH,COR)Cl(PMe,),l intermediate can be isolated, and is clearly analogous to the indium system described in Section 8. Scheme 20 56 SUNDUS HENDERSON AND RICHARD A. HENDERSON A variety of reactions, such as the co-catalysed hydrogenation of aldehydes and the rhodium-catalysed decarbonylation, hydroacylation, hydrogenations and hydroformylation of aldehydes may involve the “oxidative addition” of aldehydes to the metal centre. Furthermore, although the addition of aldehydes to tr~ns-[RhCl(CO)(PPh,)~] (Landvatter and Rauchfuss, 1982), [Ir(PMe,),]+ (Thorne, 1980) and [RhCI(PMe,),] (Milstein, 1982) has been shown to yield cis-hydridoacyl-complexes, it is not clear that any of these reactions involve the nucleophilicity of the metal.
A much more reasonable pathway involves electrophilic displacement, one-centre concerted addition and two-centre addition. Clearly factors such as the degree of coordinative unsaturation and the thermodynamics of the reaction (attempting to trade-off the strength of the C-H bond for the M-C and M-H bonds) are of prime importance in activating carbon-hydrogen bonds. , 1984). Thus the complexes discussed in this section will not be the same as those encountered so far in this review. , 1980; Green, 1978; Janowicz and Bergman, 1982).