6852-46-6Relevant academic research and scientific papers
Diastereoselective synthesis of optically active rotaxane amine N-oxides via through-space chirality transfer
Xu, Kun,Nakazono, Kazuko,Takata, Toshikazu
, p. 4356 - 4359 (2016)
Selective synthesis of optically active rotaxane amine N-oxides was achieved with high diastereoselectivity via the effective through-space chirality transfer. Oxidation of tert-amine moiety on axle component of rotaxane with an optically active wheel com
On the preparation of amine N-oxides by using dioxiranes
Ferrer, Marta,Sanchez-Baeza, Francisco,Messeguer, Angel
, p. 15877 - 15888 (2007/10/03)
The reaction of heterocyclic aromatic amines, anilines and tertiary amines with dimethyldioxirane (DMD) was examined. Treatment of heterocyclic aromatic amines and anilines with a slight excess of DMD at 0°C afforded the corresponding N-oxides in quantitative conversion yields. In addition, the oxidation was chemoselective in the presence of carbon-carbon double bonds. On the other hand, most of the tertiary amines assayed did afford also quantitative yields of the corresponding N. oxides, although reaction conditions, in particular regarding the amount of DMD required, depended on each substrate. Additional studies carried out on selected substrates suggested that certain N-oxides derived from tertiary amines deactivate DMD.
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.
Deprotonation de N-oxydes d'amines aliphatiques: schema reactionnel general et nouvelle synthese de pyrrolidines
Beugelmans, Rene,Benadjila-Iguertsira, Leila,Chastanet, Jacqueline,Negron, Guillermo,Roussi, Georges
, p. 725 - 734 (2007/10/02)
Amine oxides, 1, 5, 10, 15, 21, 23, when treated by lithium diisopropylamide undergo deprotonation.Monodeprotonation gives rise either to secondary amines and benzaldehyde resulting from the hydrolysis of an intermediate immonium (I) or to hydroxylamines via a Stevens-like rearrangement observed for the first time on an amine oxide.Double deprotonation gives an immonium ylid (Y) which, depending upon the structure of the initial tertiary amine yields either "head to head" piperazines (biradical-like behavior of (DD)) or aziridines.The immonium ylid (Y5) derived from trimethylamine oxide, whose formation and reactivity are reported for the first time, has remarkable property of undergoing cycloaddition reactions with unactivated olefins, leading to a new and efficient synthesis of various pyrrolidines.
