By D. Bethell (ed.)
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Additional resources for Advances in Physical Organic Chemistry, Vol. 23
HENDERSON The addition of acyl halides to trans-[IrCI(CO)(PMe,Ph),] also occurs with a trans-stereochemistry as shown in (29) (Deeming and Shaw, 1969; Kubota and Blake, 1971; Collman and Sears, 1968). s-[lrCI(CO)(PMe~Ph)~] + RCOBr - /-,'y R,C40 PhMe,P oc (29) PMe2Ph Br Further studies on these types of reactions, but with the more stericallydemanding PMe,Bu' ligand have shown that trans-addition of alkyl and acyl halides and cis-addition of allyl chloride are still the exclusive reaction modes (Shaw and Stainbank.
Finally the reaction of a-bromocamphor with isotopically-labelled [2HFe(CO),]- gives rise to camphor-3-exo-d as shown in ( I 6). This result &;: . & L O I*HFc(C'O)J Br (16) H has been interpreted (Alper, 1975) in terms of an S,2 attack at the carbon atom, with inversion of configuration. As discussed before, however, in the absence of any evidence concerning the sterkochemistry of the subsequent cleavage, this conclusion must remain tentative. 22 SUNDUS HENDERSON AND RICHARD A. HENDERSON REACTIONS O F C O O R D I N A T I V E L Y - U N S A T U R A T E D COMPLEXES For the reactions of coordinatively-saturated nucleophiles with alkyl halides, the overwhelming evidence is that they proceed with inversion of configuration at the carbon atom as expected for an SN2-typereaction.
The influence of the alkyl group on the reactivity has been shown to decrease with increasing chain-length. O). The close similarity between these relative rates and the analogous reactions of iodide (although the latter were studied in acetone at 30°C) was considered indicative of the nucleophilic character of the former reactions (Schrauzer and Deutsch, 1968). The surprisingly large difference between the reactivity of the methyl and ethyl halides both in the above study and in the reactions of [(q5-C5H5)Ir(CO)(PPh,)], where Me1 reacts 400-1200 times faster than EtI, has been ascribed predominantly to the steric restrictions of the ethyl group (HartDavis and Graham, 1970).
Advances in Physical Organic Chemistry, Vol. 23 by D. Bethell (ed.)