Sulfoxides thiocarbonyl ylide generation

The thermolysis of bis[(trimethylsilyl)methyl]sulfoxides (27) at 100 °C in hexamethylphosphoramide (HMPA) results in the elimination of hexamethyldisi-loxane, and thiocarbonyl ylides appear as reactive intermediates (53). This protocol allows the generation of the parent species la, as well as monosubstituted and alkylidene-substituted representatives such as lb and Ic, which are difficult to obtain by other methods (Scheme 5.9). 

Bis(trimethylsilylmethyl)sulfoxides can be employed in the thermal generation of thiocarbonyl ylides with loss of the inert hexamethyldisiloxane. As with the fluoride... 

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