33499-37-5

Upstream product

• 3717-24-6 4-chlorobenzaldehyde oxime 
• 77-78-1 dimethyl sulfate 
• 593-56-6 N-methoxylamine hydrochloride 
• 104-88-1 4-chlorobenzaldehyde 
• 2446-51-7 N-methoxybenzamide 

Downstream Products

• 54615-16-6 N-(4-chlorobenzyl)-O-methyl-hydroxylamine 
• 104-86-9 4-chlorobenzylamine 
• 91222-72-9 (z)-1-amino-1-(p-chlorophenyl)-2-(2-pyridyl)ethene 
• 91222-68-3 trans-2-(p-chlorophenyl)-3-(2-pyridyl)aziridine 

Relevant academic research and scientific papers

Method for synthesizing oxime ether compound based on C-N bond breakage

The invention relates to a method for synthesizing an oxime ether compound based on C-N bond breakage. The method comprises the step of making a compound shown in equation (1) and a compound show in equation (2) react in the presence of peroxide and an organic solvent to obtain the oxime ether compound as shown in formula (3), and reaction expression is shown in the description. According to the method, synthesis path is short, starting materials are simple, reaction condition is mild, the peroxide is cheap and free of pollution, substrate range is wide, products are easy to separate, and adaptability is high when reaction is amplified to be at the gram grade.

Stereoselective Synthesis of trans-2-Aryl-3-(2-pyridyl)aziridines from an α-Silyl Carbanion

Five para-substituted benzaldehyde oxime O-methyl ethers (3) reacted with 2-(trimethylsilylmethyl)pyridine (1) in the presence of lithium di-isopropylamide (LDA) in tetrahydrofuran to give the corresponding trans-2-aryl-3-(2-pyridyl)aziridines (4) in high yield (80, 85, 60, 58, and 74percent, respectively), with small amounts of (Z)-1-amino-1-aryl-2-(2-pyridyl)ethenes (5), and N',N'-di-isopropylbenzamidines (7) as byproducts.The yields of compounds (4) and (5) and their ratio were considerably influenced by experimental conditions (especially molar ratio and the addition method of the reactants).When treated with LDA, compounds (3) were quantitatively converted into benzonitriles, which reacted with anion (2) to give enamines (5) after elimination of a trimethylsilyl group from the corresponding N-trimethylsilyl derivatives, or with additional LDA to give the benzamidine (7); aziridines (4) were not transformed into enamines (5) by the action of LDA.On the basis of these results, a reaction mechanism has been discussed for the formation of compounds (4).