115225-33-7Relevant articles and documents
Weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis
Park, Jin,Park, Sehoon,Jang, Gwang Seok,Kim, Ran Hui,Jung, Jaehoon,Woo, Sang Kook
supporting information, p. 9995 - 9998 (2021/10/06)
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.
[Bmim]BF4-immobilized rhenium-catalyzed highly efficient oxygenation of aldimines to oxaziridines using solid peroxides as oxidants
Jain, Suman L.,Singhal, Sweety,Sain, Bir
, p. 2930 - 2935 (2008/02/02)
Various rhenium-based catalysts immobilized in [bmim]BF4 were found to be efficient for oxygenation of various aldimines to the corresponding oxaziridines in excellent yields under mild conditions using solid peroxides like UHP, SPC and SPB as oxidants. Among the various rhenium-based catalysts studied, MTO was found to be most efficient. The reusability and recyclability of MTO immobilized in [bmim]BF4 was established by using it for three subsequent cycles for oxygenation of benzylidine-tert-butylamine using UHP as oxidant.
An environmentally friendly oxidation system for the selective oxygenation of aldimines to oxaziridines with anhydrous TBHP and alumina-supported MoO 3 as a recyclable heterogeneous catalyst
Singhal, Sweety,Jain, Suman L.,Prasad,Sain, Bir
, p. 2051 - 2054 (2008/02/04)
A highly efficient and selective protocol for the oxygenation of various aldimines to oxaziridines, which proceeds in excellent yields with enhanced selectivity by using alumina-supported M0O3 as a recyclable heterogeneous catalyst and anhydrous TBHP as the ultimate oxidant, is described. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Oxidation of Imines to Oxaziridines catalysed by Transition Metal Complexes using Molecular Oxygen as the Terminal Oxidant
Martiny, Lars,Joergensen, Karl Anker
, p. 699 - 704 (2007/10/02)
The metal-catalysed oxidation of imines using molecular oxygen as the terminal oxidant and aldehydes as co-reductants has been studied.Different transition metal complexes have been tested as catalysts and it is found that cobalt complexes can catalyse the selective oxidation of imines to oxaziridines.The cobalt-catalysed oxidation of imines to oxaziridines is dependent on the aldehyde used as co-reductant; thus, the presence of aliphatic aldehydes leads to a smooth oxidation, whilst in the presence of aromatic aldehydes there was no reaction.The oxidation proceeds well for imines with aliphatic and aromatic substituents attached to the nitrogen and carbon atom, respectively.The electronic nature of the oxygen atom transferred in these reactions, investigated using thianthrene 5-oxide as a probe, was found to be electrophilic in character.The mechanistic aspects of the cobalt-catalysed oxidation of imines to oxaziridines, probably involving a peroxyacyl cobalt intermediate, are discussed.
PHASE-TRANSFER CATALYTIC SYNTHESIS OF OXAZIRIDINES
Bulachkova, A. I.,Koldobskii, G. I.,Drozdetskii, A. G.,Tereshchenko, G. F.
, p. 632 - 636 (2007/10/02)
The phase-transfer catalytic oxidation of imines is a general method for the preparation of oxaziridines with various structures.Oxone (2KHSO5*KHSO4*K2SO4) and perbenzoic acid in combination with such phase-transfer catalysts as benzyltriethylammonium chl
Imines and Derivatives. Part 24. Nitrone Synthesis by Imine Oxidation using either a Peroxyacid or Dimethyldioxirane
Boyd, Derek R.,Coulter, Peter B.,McGuckin, M. Rosaleen,Sharma, Narain D.,Jennings, W. Brian,Wilson, Valerie E.
, p. 301 - 306 (2007/10/02)
The oxidation of N-alkyl imines by m-chloroperoxybenzoic acid to yield nitrones was facilitated by (i) the presence of C-aryl substituents, (ii) steric inhibition of attack at the imino C-atom, (iii) electron donating para-substituents on the C-aryl substituent, (iv) non-hydroxylic solvents, (v) optimal conjugation between C-aryl substituents and the imino group, and (vi) less bulky N-alkyl groups. The oxidation of N-alkyl imines by dimethyldioxirane (DMD) in dichloromethane-acetone solution yielded nitrones without evidence of oxaziridine formation.The yields of isolated nitrones were higher for C,C-diaryl imines and for imines bearing less bulky N-alkyl substituents.N-H substituted ketimines were found to yield oximes after reaction with dimethyldioxirane.
NORMAL, ABNORMAL AND PSEUDO-ABNORMAL REACTION PATHWAYS FOR THE IMINE-PEROXYACID REACTION
Boyd, Derek R.,Coulter, Peter B.,Sharma, Narain D.,Jennings, Brian W.,Wilson, Valerie E.
, p. 1673 - 1676 (2007/10/02)
Steric and mesomeric effects have a marked influence upon the formation of oxaziridine (normal pathway) or nitrone (abnormal pathway) products from the imine-peroxyacid reaction; n.m.r. studies of the thermal isomerization of oxaziridines to nitrones prov
