90524-29-1Relevant academic research and scientific papers
Base-promoted Rearrangement of Siloxyammonium Salts: a New Method of Dealkylation of Tertiary Amines via Their N-Oxides
Okazaki, Renji,Tokitoh, Norihiro
, p. 192 - 193 (1984)
Siloxyammonium salts prepared from tertiary amine N-oxides and trialkylsilyl trifluoromethanesulphonate undergo rearrangement in the presence of strong bases to give α-siloxyamines, which can be converted into secondary amine derivatives.
Silicon Polonovski Reaction. Formation and Synthetic Application of α-Siloxy Amines
Tokitoh, Norihiro,Okazaki, Renji
, p. 3291 - 3298 (2007/10/02)
A new and versatile synthetic intermediate, α-siloxy amine was prepared in situ by the base-promoted rearrangement of a siloxyammonium salt obtained by treatment of a tertiary amine N-oxide with trialkylsilyl trifluoromethanesulfonate.The best combination of the base and silylating reagent was found to be methyllithium and t-butyldimethylsilyl trifluoromethanesulfonate.The reactions of α-siloxy amines with acyl halides and haloformates gave the corresponding amides and carbamates in moderate to good yields, respectively.Treatment of α-siloxy amines with acetic acid resulted in a direct dealkylation to free secondary amines.Fluoride induced alkylation of α-siloxy amines using alkyl halides as electrophiles leading to tertiary amines was also examined and demonstrated to be a new transalkylation method of amines.
A NEW SYNTHESIS OF α-CYANOAMINES. LEWIS ACID PROMOTED NUCLEOPHILIC SUBSTITUTION OF α-SILOXYAMINES USING TRIMETHYLSILYL CYANIDE
Tokitoh, Norihiro,Okazaki, Renji
, p. 241 - 242 (2007/10/02)
α-Siloxyamines obtained from tertiary amines via their N-oxides were treated with titanium tetrachloride and trimethylsilyl cyanide to give α-cyanated tertiary amines in good yields.
