Reactions involving the heterolytic cleavage of carbon–element σ-bonds by Grignard reagents

The reactions involving the heterolysis of the C–O, C–C, C–N, C–S, C–Cl, etc. bonds by organomagnesium compounds are examined and the nature of this interesting phenomenon is analysed. On the basis of the analysis of the characteristic features of the cleavage under discussion, it is shown that the heterolysis of the carbon–element bond is, firstly, a general reaction for all classes of organic compounds (provided that two conditions are observed: the substrate molecule must fragment into two stable species – a carbonium ion and an anion – and the strength of the Lewis acid properties should be adequate for the occurrence of the above reaction) and, secondly, the heterolysis of the carbon–element bond is one of the independent pathways in the reactions of the Grignard reagents.
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