Alkylmagnesium thiolates

SR Alkylmagnesium thiolate Alkyl(alkylthio)magnesium or alkanethiolatoalkylmagnesium... 

Detailed reviews on the structures of organomagnesium compounds and the constitution of their solutions have been published [D, 1, 2]. These references, especially the first two, also cover alkylmagnesium hydrides, amides, alkoxides and thiolates. However, while all of these compounds are of intrinsic interest, they are little used in synthesis. 

For application in synthesis, the most important of these are those where X = halogen and Y = alkyl the transformation of Grignard reagents into dialkylmagnesium compounds. Other transformations of this type are valuable for preparing alkylmagnesium hydrides (Y = H), alkoxides (Y = OR ), carboxylates (Y = OCOR ), amides (Y = NR 2, thiolates (Y = SR ), etc., but since most of these products are not extensively employed in synthesis these transformations are summarized only briefly. 

Although other methods are available for synthesizing alkylmagnesium dialkylamides, alkoxides and thiolates, the reaction of a dialkylmagnesium compound with a secondary amine, an alcohol, or a thiol, provides a convenient general method. Some examples are summarized in Table 3.11. 

With a dialkylmagnesium compound, one equivalent of the proton donor gives an alkylmagnesium alkoxide (thiolate, amide) (see Section 3.4.4), whereas 0.5 equivalent gives the magnesium alkoxide (thiolate, amide) ... 

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