Alkylmagnesium bromide salts

Alkylmagnesium bromides and alkyllithiums have been used to prepare alkanesul-phinate salts, which have then been oxidized to the sulphonyl bromides in high yields578,579,581. This is an excellent synthetic route to sulphonyl halides that are not easily obtained by other routes. 

Reactions of thoiminium salts, generated in situ from thioamides and methyl triflate (MeOTf), with two different alkylmetals such as alkynyllithiums and alkylmagnesium bromides have been studied. The two different organometallic reagents have been nucleophilically introduced to the carbon atom of the thiocarbonyl group of thiamides to afford tertiary propargylamines in one-pot procedure (Scheme 36). ... 

Alkyl metals are not suitable for the metallation of tiiese compounds. For example, BuaU reacts at -78 C on the seletuum atom of selenonium salts and produces a novel organolithium in which the carb-aruonic center is more stabilized (Scheme 50, a and b), whereas alkylmagnesium bronudes and chlmides unexpectedly lead to decyl bromide and chloride respectively on reaction with decyl phenyl selenrme (Scheme 50, c). 

Alkylmagnesium halides can also be used. Functionalized alkylzinc bromides [56] such as 30-33 (Scheme 4.7), as well as benzylzinc chlorides [55, 57], can be prepared starting from the corresponding organic halides through in situ reduction involving Mg(0) in the presence of Zn(II) salts. 

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