HSAB organometallics

The classification of metals, their salts, and organometallic compounds, based on the Principle of Hard-Soft Acids and Bases (HSAB) of Pearson [112,116,156-158], is discussed in detail in Sec. 1.2.2. 

An organometallic can react with a metal salt to produce a new organometallic and a new salt in the process called transmetallation. As expected from the HSAB principle, this equilibrium favors the formation of the more covalent organometallic from the softer pair and the more ionic salt from the harder pair. Transmetallation allows the conversion of a reactive organometallic into a more covalent, less reactive organometallic ... 

HSAB principle in reactions of organometallic derivatives 85TI. 

Organometallic agents attack the thionic S leading to a reductive alkylation (113-115). Although it has been demonstrated that the Grignard reaction proceeds via free radical intermediates (116), it is certainly subject to orbital control and obeys the HSAB principle. Hudson (117) has discussed the behavior of such interacting radicals. 

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