Sulfoxides reactions with organomagnesium

Reactions of organomagnesium compounds with sulfoxides often result in ligand exchange [31], and may be complicated by a- or ortho metallation. However, in some cases, notably with 2-pyridyl aryl sulfoxides, reactions with arylmagnesium halides give useful yields of products from displacement of the aryl sulfoxido group [32, 33], e.g. [32]... 

Allenyl and 1- and 2-alkynyl sulfoxides have also been prepared by reaction of organomagnesium halides with sulfinate ester 19. 1-Alkynyl p-tolyl sulfoxides were prepared in good yield from 1-alkynylmagnesium halides plus ester 19 in toluene (equation ll)63. The corresponding organolithium compound was unsatisfactory as a... 

The formation of a-substituted thiolanes 203 in 40-70% yields was observed by reactions of trimethylene sulfoxide with organomagnesium compounds (Eq. 49). ... 

Although in most cases reactions of organomagnesium compounds with sulfoxides give mixtures resulting from ligand exchange and/or deprotonation, examples have recently been described where... 

Sulfoxides containing a methylsulfinyl group react with organomagnesium halides to give sulfides. 24,125 The reaction was suggested to involve deprotonation, formation of a methylydene-sulfonium intermediate and addition of the alkyl Grignard on the a-carbon.l25... 

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