91222-70-7

Basic information

• Product Name: Pyridine, 2-[3-(4-methoxyphenyl)-2-aziridinyl]-, trans-
• CAS NO: 91222-70-7
• Molecular Formula: C14H14N2O
• Molecular Weight: 226.278
• Mol File: 91222-70-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Pyridine, 2-[3-(4-methoxyphenyl)-2-aziridinyl]-, trans-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 2-[3-(4-methoxyphenyl)-2-aziridinyl]-, trans-(91222-70-7)
• EPA Substance Registry System: Pyridine, 2-[3-(4-methoxyphenyl)-2-aziridinyl]-, trans-(91222-70-7)

Safety Data

• Hazardous Substances Data: 91222-70-7(Hazardous Substances Data)

Upstream product

• 70286-37-2 4-methoxybenzaldehyde O-methyl oxime 
• 129760-63-0 C₉H₁₄NSi^(1-)*Li⁽¹⁺⁾ 
• 123-11-5 4-methoxy-benzaldehyde 
• 17881-80-0 (2-picolyl)trimethylsilane 
• 70286-37-2 4-methoxy-benzaldehyde-(O-methyl-seqtrans-oxime ) 

Relevant articles and documents

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).

REACTION OF Α-SILYL CARBANION WITH OXIME ETHERS

In the presence of LDA, 2-(trimethylsilylmethyl)pyridine reacts with p-substituted benzaldoxime methyl ethers to give stereoselectively trans-2-aryl-3-(2-pyridyl)aziridines and (z)-1-amino-1-aryl-2-(2-pyridyl)ethenes.From the temperature dependent 1H-nmr spectra of trans-2-phenyl-3-(2-pyridyl)aziridine, ΔF* was estimated to be about 14 kcal/mol at the coalescence temperature (Tc = 0 deg C).