22746-90-3Relevant academic research and scientific papers
A Stereochemical Investigation of 2-Methyl- and 2,5-Dimethyl-3-phenyl-1,3-oxazolidines using NMR
Nishiyama, Tomihiro,Nishikawa, Takahiro,Yamada, Fukiko
, p. 1687 - 1690 (2007/10/02)
The stereochemical properties of two 2-methyl-3-phenyl-1,3-oxazolidines and two of its 5-methyl substituted and four of its 2,5-dimethyl substituted derivatives have been investigated by pmr and cmr methods.The compounds of 2,5-dimethyl-3-phenyl-1,3-oxazo
Reaction of N,N-Dimethylaniline Derivatives with Cumene Hydroperoxide. Oxazolidine Formation via Addition of α-Aminomethyl Radicals to Formaldehyde
Humphreys, Robert W. R.
, p. 1483 - 1487 (2007/10/02)
The reactions of N,N-dimethylaniline derivatives (1) with cumene hydroperoxide in acetonitrile at 100 deg C produce significant amounts of the corresponding N-aryloxazolidine (6).Oxazolidine formation occurs by addition of α-aminomethyl radicals (7) to formaldehyde to give the alkoxy radical (8), followed by intramolecular 1,6 H-atom abstraction, oxidation, and cyclization.The results of labeling experiments and the dependence of the oxazolidine yield on the formaldehyde concentration support this mechanism.Alkoxy radical 8 was generated by an alternative route anddoes give the oxazolidine.Radical addition to the carbonyl carbon of formaldehyde is a reflection of the electron-rich, nucleophilic nature of the α-aminomethyl radical 7 and rapid trapping of the resulting alkoxy radical 8 via intramolecular H-atom abstraction through a six-membered transition state.
