Indirect reduction of halides and isotopic labelling via organomagnesium compounds

1 INDIRECT REDUCTION OF HALIDES AND ISOTOPIC LABELLING VIA ORGANOMAGNESIUM COMPOUNDS 

An example of indirect reduction via an organomagnesium compound is a well-described synthesis of n-pentane [1]  

Examples involving metal-halogen exchange (see Section 3.2.2) rather than reaction with magnesium have also been described, e.g. [2] 

Reaction with deuterium oxide, O-deuterated alcohols or acids is commonly used to provide evidence for the formation of organomagnesium compounds (e.g. see Ref. [3]). Although the presence of water normally inhibits the reaction of organic halides with magnesium, it is noteworthy that under appropriate conditions a Barbier procedure was successful [4]  

For preparative deuterium or tritium labelling, organomagnesium compounds are less generally used than organolithium compounds, but similar considerations should apply [5]. In the following example a remarkably high degree of tritium incorporation was achieved [6]  

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