Silicon reagents in chemical transformations: the concept of 'counterattack reagent'

Heteroatom-containing reagents Me3SiOOSiMe3, Me3SiSiMe3, and (Me3Si)(3)N ar e utilized for the performance of efficient chemical transformations in 'on e-flask.' Oxidative desulfonylation of organic sulfones to the correspondin g carbonyl compounds by use of Me3SiOOSiMe3 and n-BuLi involves a simple 'c ounterattack process'. Double functional group transformation of a nitroalk ene to a carbonyl nitrile with Me3SiSiMe3 went through a 'tandem double-cou nterattack process'. Persilylation of hydrazine with Me3SiSiMe3 in the pres ence of KH took place by a 'consecutive triple-counterattack process'. Poly merization of trimethyl phosphate with (Me3Si)(3)N in the presence of n-BuL i represents an extreme example: 'multiple-counterattack process'. Use of M e3SiOOSiMe3, Me3SiSiMe3, and (Me3Si)(3)N as 'counterattack reagents' allows the accomplishment of complicated chemical transformations with minimal op erations and often gives the desired products in good yields.