3683-70-3

Upstream product

• 2325-27-1 N-phenyltriphenyliminophosphorane 
• 4541-87-1 cis-1-phenylpropene oxide 
• 119487-86-4 (E)-2-methyl-1,3-diphenyl-2-(p-tolylsulfinyl)aziridine 
• 538-51-2 benzylidene phenylamine 
• 1009795-12-3 C₁₉H₂₄NO₄P 
• 119487-82-0 [(1S,2S)-2-Chloro-1-phenyl-2-(toluene-4-sulfinyl)-propyl]-phenyl-amine 
• 766-90-5 cis-1-phenyl-1-propylene 
• 119487-86-4 (2R,3R)-2-Methyl-1,3-diphenyl-2-((S)-toluene-4-sulfinyl)-aziridine 
• 917-54-4 methyllithium 
• 72374-71-1 N-(2,2-dichloro-1-phenyl-1-propylidene)aniline 
• 119487-82-0 [(1S,2S)-2-Chloro-1-phenyl-2-((S)-toluene-4-sulfinyl)-propyl]-phenyl-amine 

Relevant academic research and scientific papers

Ring splitting of azetidin-2-ones via radical anions

The radical anions of azetidin-2-ones, generated by UV-irradiation in the presence of triethylamine, undergo ring-splitting via N-C4 or C3-C4 bond breaking, leading to open-chain amides. This reactivity diverges from that found for the neutral excited states, which is characterised by α-cleavage. The preference for β-cleavage is supported by DFT theoretical calculations on the energy barriers associated with the involved transition states. Thus, injection of one electron into the azetidin-2-one moiety constitutes a complementary activation strategy which may be exploited to produce new chemistry.

Novel aziridination of α-halo ketones: an efficient nucleophile-induced cyclization of phosphoramidates to functionalized aziridines

A novel and efficient aziridination of α-halo ketones is reported. The reaction of α-halo ketones with diethyl N-arylphosphoramidates affords diethyl N-aryl-N-(2-oxoalkyl)phosphoramidates which undergo reductive (H--induced) cyclization with so

Generation of aziridinyllithiums from sulfinylaziridines with tert- butyllithium: Properties, reactivity, and application to a synthesis of α,α-dialkylamino acid esters and amides including an optically active form

Aziridinyllithiums were generated from sulfinylaziridines by a sulfoxide-lithium exchange reaction of sulfoxides with tertbutyllithium at low temperature. The generated aziridinyllithiums were found to be stable in THF at below -30°C and they are reactive with several electrophiles such as carbonyl compounds, ethyl chloroformate, and phenyl isocyanate. The reactivities of the aziridinyllithiums having several alkyl groups were investigated. As an extension of this method, a synthesis of α,α- dialkylamino acid esters, including an optically active form, and amides was realized via the aziridinyllithiums. N-Non substituted α,α-dialkylamino acid esters were synthesized starting from N-(4-methoxyphenyl) aldimine. (C) 2000 Elsevier Science Ltd.

Generation of Aziridinyllithiums from Sulfinylaziridines by the Ligand Exchange Reaction of Sulfoxides with tert-Butyllithium: Their Properties and An Application to Asymmetric Synthesis of α-Dialkylamino Acid Ester

Aziridinyllithiums were generated from sulfinylaziridines by the ligand exchange reaction of sulfoxides with tert-butyllithium.The aziridinyllithiums were found to be stable in THF at below -30 deg C and reactive with several electrophiles such as carbony

Zinc(II)-catalysed transformation of epoxides to aziridines

The Lewis acid-catalysed transformation of epoxides to aziridines with iminophosphoranes as the nitrogen-fragment donor has been investigated. Of the Lewis acids tested, zinc(II) complexes had the best catalytic properties. The method works best for terminal and cyclic epoxides, internal epoxides being less reactive. Of the various iminophosphoranes employed N-(triphenylphosphoranylidene)-aniline and -isopropylamine were the most successful. The zinc(II)-catalysed reaction has been studied for chiral styrene oxides for which the enantiomeric excess of the aziridine produced is dependent on the reaction time. The reaction of achiral and chiral styrene oxides and N-(triphenylphosphoranylidene)aniline in the presence of a zinc(II) complex having a chiral ligand has been investigated as has the reaction for cis-deuteriostyrene oxide in order to obtain information about the stereochemical outcome of the reaction. A mechanism for the title reaction is discussed on the basis of the experimental results.

Stereospecific Desulfinylation of Sulfinylaziridines with Alkylmetals: A Novel Synthesis Including Asymmetric Synthesis of (Z)-N-Arylaziridines and Some Mechanistic Studies

Addition of the anion derived from 1-chloroalkyl p-tolyl sulfoxides 3 to N-arylimines 4 afforded chloro amines 5 in high yields with complete 1,2- and 1,3-asymmetric induction.Treatment of these chloro amines 5 with potassium tert-butoxide gave sulfinylaz

STEREOSPECIFIC DESULFINYLATION OF SULFINYLAZIRIDINES WITH ETHYLMAGNESIUM BROMIDE: A NOVEL SYNTHESIS OF (Z)-N-ARYLAZIRIDINES

A novel synthesis of (Z)-N-arylaziridines was realised by the stereospecific desulfinylation of (E)-(N-aryl)sulfinylaziridines which were synthesized from 1-chloroalkyl p-tolyl sulfoxides and N-arylimines in high yields.

Stereospecific Synthesis of N-Substituted cis-2-Aryl-3-alkylaziridines

A convenient stereospecific synthesis of N-substituted cis-2-aryl-3-alkylaziridines is reported, by reaction of N-alkyl or N-aryl α,α-dichloroalkyl aryl ketimines with lithium aluminum hydride in ethereal medium.The mechanism involves the addition of hydr