Abstract
Various primary nitro compounds were reacted sequentially with KH and Me 3 SiSSiMe 3 in THF to give thiohydroxamic acids in 56-92% yields. By the same strategy, a thiohydroxamic acid was obtained in 50% yield by treatment of trans-β-nitrostyrene with i-PrSLi in THF and then with Me 3 SiSSiMe 3 . Reaction of primary nitro compounds with n-BuLi and then with MeSSiMe 3 or PhSSiMe 3 produced the corresponding thiohydroximates in 61-78% yields. Secondary nitro compounds were converted to oximes in 68-96% yields by reaction with KH and Me 3 SiSSiMe 3 or MeSSiMe 3 in THF or 1,4-dioxane. In these "one-flask" reactions, thiosilanes Me 3 SiSSiMe 3 , MeSSiMe 3 , and PhSSiMe 3 acted as "counterattack reagents". © 1990.