825-81-0Relevant academic research and scientific papers
Synthesis of Halogenated Anilines by Treatment of N, N-Dialkylaniline N-Oxides with Thionyl Halides
Reed, Hayley,Paul, Tyler R.,Chain, William J.
, p. 11359 - 11368 (2018/08/06)
The special reactivity of N,N-dialkylaniline N-oxides allows practical and convenient access to electron-rich aryl halides. A complementary pair of reaction protocols allow for the selective para-bromination or ortho-chlorination of N,N-dialkylanilines in up to 69% isolated yield. The generation of a diverse array of halogenated anilines is made possible by a temporary oxidation level increase of N,N-dialkylanilines to the corresponding N,N-dialkylaniline N-oxides and the excision of the resultant weak N-O bond via treatment with thionyl bromide or thionyl chloride at low temperature.
Deoxygenation of tertiary amine N-oxides under metal free condition using phenylboronic acid
Gupta, Surabhi,Sureshbabu, Popuri,Singh, Adesh Kumar,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
supporting information, p. 909 - 913 (2017/02/15)
A simple and efficient method for the deoxygenation of amine N-oxides to corresponding amines is reported using the green and economical reagent phenylboronic acid. Deoxygenation of N,N-dialkylaniline N-oxides, trialkylamine N-oxides and pyridine N-oxides were achieved in good to excellent yields. The reduction susceptible functional groups such as ketone, amide, ester and nitro groups are well tolerated with phenylboronic acid during the deoxygenation process even at high temperature. In addition, an indirect method for identification and quantification of tert-amine N-oxide is demonstrated using UV–Vis spectrometry which may be useful for drug metabolism studies.
OXIDATION OF AMINES WITH 4a-FlEt-OOH: AN ENZYME MODEL OF FAD-CONTAINING MONOOXYGENASE
Oae, Shigeru,Asada, Kaoru Ogawa,Yoshimura, Toshiaki,Fujimori, Ken
, p. 189 - 194 (2007/10/02)
Unlike the real enzyme, FAD-containing monooxygenase, 4a-FlEt-OOH, oxidizes most of common primary, secondary and tertiary water-soluble amines, such as N-methylmorpholine and n-octylamine.Both kinetic rates and products of the oxidation were obtained.The plots of rates vs. pKa values gave three different correlations lines depending upon the types of amines.
THE MECHANISTIC MODE OF OXIDATION OF SUBSTITUTED N,N-DIMETHYLANILINES, THIOANISOLES, AND METHYL PHENYL SULFOXIDES BY 5-ETHYL-4a-HYDROPEROXY-3-METHYL-LUMIFLAVIN (4a-FlEt-OOH)
Oae, Shigeru,Asada, Kaoru,Yoshimura, Toshiaki
, p. 1265 - 1268 (2007/10/02)
In the oxidation of the title compounds, 5-ethyl-4a-hydroperoxy-3-methyl-lumiflavin (4a-FlEt-OOH), was found to be an electrophilic oxidant similar to m-chloroperoxybenzoic acid.However, the stereoselectivity of the oxidation of cyclic sulfides to the corresponding sulfoxides by 4a-FlEt-OOH was less pronounced than that of the oxygenation with flavin-containing monooxygenase.
