Acidolysis of organometallic compounds

Many electrophilic reagents are capable not only of electrophilic attack at the carbon atom of the C-M bond, but also of nucleophilic attack at the metal atom of the C-M bond. It is such nucleophilic attack that gives rise to the mechanisms SE2(cyclic) and SE2(co-ord). Dessy et al.12,13 have several times stressed the importance of internal nucleophilic assistance by the electrophilic reagent in reaction mechanisms of organometallic compounds, and it is the account by Dessy and coworkers13 of the acidolysis of triethylboron that is probably the classic report in this field. 

The difficulties over the constitution of organomagnesium compounds mentioned above, prompted Abraham and Hill22 to study the kinetics of acidolysis of reactive organometallic compounds of well-defined constitution. Dialkylzincs are monomeric substances23 which may be purified by distillation, and should therefore be more suitable substrates. Acidolysis of di- -propylzinc by the weak acids p-toluidine and cyclohexylamine at 76 °C in solvent diisopropyl ether was shown to follow kinetics compatible with the two competitive consecutive second-order reactions (15) (R = Pr", R = p-tolyl or cyclohexyl) and (16) (R = Pr", R = p-tolyl or cyclohexyl),... 

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