Antimony—hydrogen bonds reactions with

Hydrocarbons undergo related reaction.s in the super-acid media, such as fluorosuiphuric acid and antimony pentachloride. It has been suggested that the initial one-electron processes during the electrochemical oxidation of alkanes in fluorosuiphuric acid involve a protonated carbon-hydrogen bond with formation of a carbon radical and release of two protons [15]. 

In the reaction with halides of the less electropositive metals such as mercury,79 arsenic,80- 81 antimony,82 and indium,83 a stannane provides nucleophilic hydrogen and gives the new metal hydride (equation 15-27). Free radical inhibitors may be added to repress radical reaction of vinyl reactants. The preparation of vinylmercury hydride by this route involves the unusual use of tributyltin chloride as a solvent (equation 15-28).79 On the other hand, in the reactions of tributyltin hydride with Grignard reagents, RMgX, the hydrogen behaves as an electrophile towards R, and the Sn-Mg bonded compounds are formed.84... 

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