128072-71-9

Basic information

• Product Name: 2-tert-Butyl-3-(2-methoxy-phenyl)-oxaziridine
• Synonyms: 2-tert-Butyl-3-(2-methoxy-phenyl)-oxaziridine
• CAS NO: 128072-71-9
• Molecular Weight: 207.272
• Mol File: 128072-71-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-tert-Butyl-3-(2-methoxy-phenyl)-oxaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-tert-Butyl-3-(2-methoxy-phenyl)-oxaziridine(128072-71-9)
• EPA Substance Registry System: 2-tert-Butyl-3-(2-methoxy-phenyl)-oxaziridine(128072-71-9)

Safety Data

• Hazardous Substances Data: 128072-71-9(Hazardous Substances Data)

Upstream product

• 82632-38-0 N-tert-butyl-1-(2-methoxyphenyl)methanimine 
• 75-64-9 tert-butylamine 
• 135-02-4 ortho-anisaldehyde 

Downstream Products

• 130995-65-2 N-tert-butyl-α-(2-methoxy)phenylnitrone 
• 88105-14-0 (2-methoxyphenyl)-tert-butylamino-methanone 
• 135-02-4 ortho-anisaldehyde 

Relevant articles and documents

Weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis

The selective rearrangement of oxaziridines to amidesviaa single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis. The developed method shows excellent functional group tolerance with a broad substrate scope and good to excellent yields. Furthermore, control experiments and density functional theory (DFT) calculations are performed to gain insight into the reactivity and selectivity.

Rearrangement Reactions of Oxaziridines to Nitrones. X-Ray Crystal and Molecular Structure of N-t-Butyl-α(o-hydroxyphenyl)nitrone

Substituted N-benzylidene-t-butylamines are oxidized with m-chloroperoxybenzoic acid to oxaziridines which can rearrange to the corresponding nitrones when electron-donating groups are present in the phenyl ring.The oxaziridine-to-nitrone rearrangement, which has been considered as a 'pseudo-abnormal' reaction, can also be catalysed by Lewis acids.It has been found that the rearrangement of 2-t-butyl-3-(o-hydroxyphenyl)oxaziridine to the corresponding nitrone is of first order.The rearrangement has been investigated for different substituents in the phenyl ring, andin the case of 2-t-butyl-3-phenyloxaziridine substituted in the ortho position with electron-donating groups it has been found that the presence of protons of a Lewis acid is necessary.An X-ray structure of α-(o-hydroxyphenyl)-N-t-butylnitrone shows strong hydrogen bonding between the nitrone oxygen and the hydrogen in the hydroxy group.The oxaziridine-to-nitrone rearrangement is also analysed from a theoretical point of view using ab initio calculations.A Mulliken-population analysis of the C-O and N-O bonds in the oxaziridine ring for para-substitued 2-t-butyl-3-phenyloxaziridines shows a reduction of the C-O bond population when an electron-donating group is present in the para position of the phenyl ring compared with an electron-withdrawing group; the N-O bond populations show the reverse picture.A state-correlation diagram for the oxaziridine-to-nitrone rearrangement is also presented and the experimental and theoretical results support each other.