Reactivity of N-phenyl silylated ketenimines with electrophilic reagents

Article abstract of DOI:10.1016/S0040-4020(99)00219-7

We report the reactivity of new Cβ silylated ketenimines (4, 5, 6) and lithiated-silylated ketenimine 3 [easily generated from lithiated S-methyl- N-phenyl-trimethylsilylethanimidothioate 2] toward electrophilic reagents. Reactions of these ketenimines with strong electrophilic reagents such as sulfanyl chloride (PhSCl) gave access to new sulfanylated ketenimines. With less reactive species [benzenesulfinyl chloride (PhS(O)Cl), p-toluenesulfonyl chloride, trimethylhalosilanes, diisopropyl chlorophosphate, acetyl chloride and propylene oxide] and 3, the addition took place either on Cβ or on the nitrogen atom leading to relatively unstable functionalised ketenimines or new silylated ynamines respectively.