Advances in Physical Organic Chemistry, Vol. 23 by D. Bethell (ed.)

By D. Bethell (ed.)

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In particular it is observed that, as the coordinating capability of the solvent towards the cation (associated with Me,Sn-) increases, the proportion of inversion at the carbon centre increases. , 1978). , 1978). The reactions of cyclopropylmethyl bromide proceed via free, non-caged, radicals. The stereochemistry of the reaction is also sensitive to the countercation of Me&-. Thus the lithium salt at -70°C gives a higher proportion of the product with inverted configuration than the sodium salt.

Me - Me + + + CI, oc/ oc‘ ‘Ir’ I L CI T I‘’ IL‘ oc/ I I CI L I I I Me1 L‘ I 1 CI I /I L , OCY1‘\ Me Me L L‘ Ic1- Ic (A) 1- Me (L = monotertiary phosphine) oc’ L‘I I Scheme 12 In benzene, nucleophilic attack by the complex on Me1 yields the ion-pair, and subsequent attack by iodide at the metal yields the trans-product. THE NUCLEOPHILICITY OF METAL COMPLEXES 35 However in the more polar methanol the ion-pair can separate, and subsequent rapid reaction of iodide with trans-[IrCI(CO)(PMe,Ph),] results in halide exchange and hence the corresponding mixture of products.

The reactions of acyl halides with [FeH(CO),]- have been used to prepare aldehydes, by the (assumed) pathway shown in (50) (Cole and Pettit, 1977; THE NUCLEOPHILICITY OF METAL COMPLEXES 55 this paper contains several references to other applications of this versatile reagent). , 1972). It is not entirely clear what the exact nature of the “active” species is, but the wine colour of the solution may suggest the formation of [HFe,(CO),]- and [HFe,(CO), ,I-. The nucleophilicity of transition metal complexes towards organic molecules has found application in industrial catalysts.

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