Sulfoxide, methyl thiomethyl alkylation

The seleno derivative 1374, which can be readily prepared by reduction of di-phenyldiselenide with sodium borohydride then alkylation with chloromethyltri-methylsilane, is alkylated to 1375 to give, on oxidative hydrolysis, aldehydes 1376 in high yields, PhSe02H-H20 1377 [104], and 7 (Scheme 8.44). Alkylation of the commercially available methyl thiomethyl sulfoxide 1378 leads to mono- or dialkyl... 

Monoalkylation of the carbanion generated from methyl thiomethyl sulfoxide and 1,3-dithiane I-oxide - has been reported (Scheme 74, entry b) but reexamination of both reactions - proved unsatisfactory under conditions similar to those previously described or slightly modified. Neither the stepwise- nor the one-pot dialkylation was successful at 20 C, but the latter reaction was apparently achieved by Schill- by performing it at 50 °C with a slight excess (2.2 equiv.) of n-alkyl bromides in... 

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