79866-06-1

Upstream product

• 71260-88-3 N-phenyl-methyl(benzenesulfanyl)ketenimine 
• 134916-82-8 N-phenyl-methyl-(trimethylsilyl)ketenimine 
• 931-59-9 benzenesulfenyl chloride 
• 134948-24-6 S-methyl α-(trimethylsilyl)ethanimidothioate 

Downstream Products

• 71260-88-3 N-phenyl-methyl(benzenesulfanyl)ketenimine 

Relevant academic research and scientific papers

Reactivity of N-phenyl silylated ketenimines with electrophilic reagents

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.

Synthesis and Reactions of C-Sulphenylketenimines

The Horner-Wittig reaction of (1a,b) with phenyl isocyanate or dehydration of amides (4c-g) gave the C-sulphenylketenimines (3a-g) in moderate yields.Thermolysis of (3b) gave 2-ethoxy-3-phenylthioquinolin-4-ol (7) via intramolecular cyclization, and the r