Reactions of organic peroxides. Part XIV. Amino-peroxides from carbonyl compounds, primary amines, and hydrogen peroxide or hydroperoxide
Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39690002686
Abstract
The reaction of a number of carbonyl compounds (cyclic and acyclic) with primary amines and hydrogen peroxide gives solid α-hydroperoxy-amines, R1R2C(NHR3)·O·OH, unstable at room temperature. In such reactions cyclohexanone and hydrogen peroxide can be replaced by 1,1′-dihydroxydicyclohexyl peroxide. Treatment of these α-hydroperoxy-amines with acetic acid–acetic anhydride at room temperature yields the corresponding oxaziridines. Replacement of the hydrogen peroxide by t-butyl hydroperoxide leads to the formation of the correspondingα-t-butylperoxy-amines, R1R2C(NHR3)·O·OBut, compounds which are fairly easily converted into the imines, R1R2C![[double bond, length half m-dash]](http://scimg.chem960.com/usr/1/J39690002686.jpg)
NR3, by loss of t-butyl hydroperoxide. With acylic ketones only imines, but not t-butylperoxy-amines, could be obtained.
Recommended Literature
- [1] An aptasensor for detection of potassium ions based on RecJf exonuclease mediated signal amplification Bidou Wang,Xifeng ChenAnalyst, 2014,139, 5695-5699 10.1039/C4AN01350F
- [2] An aptamer-based keypad lock system? Yaqing Liu,Jiangtao Ren,Jing Li,Jiyang Liu,Erkang WangChem. Commun., 2012,48, 802-804 10.1039/C1CC15979H
- [3] An apparatus for determining small amounts of alchohol in sour milk and urine Analyst, 1964,89, 272-275 10.1039/AN9648900272
- [4] Acenaphthenic hopanoids, a novel series of aromatised Teresita Carrillo-Hernández,Philippe Schaeffer,Pierre AlbrechtChem. Commun., 2001, 1976-1977 10.1039/B105198A
- [5] Aggregated-fluorescent detection of PFAS with a simple chip Cheng Fang,Jinjian Wu,Zahra Sobhani,Md. Al Amin,Youhong TangAnal. Methods, 2019,11, 163-170 10.1039/C8AY02382D
- [6] An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation?? M. Sheykhan,S. Khani,S. Shaabanzadeh,M. JoafshanGreen Chem., 2017,19, 5940-5948 10.1039/C7GC03141F
- [7] Achieving crystal-induced room temperature phosphorescence and reversible photochromic properties by strong intermolecular interactions? Fuming Xiao,Mengzhu Wang,Yunxiang Lei,Wenbo Dai,Yunbing Zhou,Miaochang Liu,Wenxia Gao,Xiaobo Huang,Huayue WuJ. Mater. Chem. C, 2020,8, 17410-17416 10.1039/D0TC03980B
- [8] Aggregation-induced emission based on a fluorinated macrocycle: visualizing spontaneous and ultrafast solid-state molecular motions at room temperature via F?F interactions? Mei Zhang,Jingjing Guo,Tingting Liu,Zhanyu He,Majeed Irfan,Zujin Zhao,Zhuo ZengJ. Mater. Chem. C, 2020,8, 14919-14924 10.1039/D0TC03797D
- [9] Achieving Efficient Uranium Extraction by In-situ Ultrasonic Texturization of Commercial Fe Powder BomingZhu,HongweiWu,JieKang,XiaofangYu,TaoChen,RuCheng,GuolinYang,WencaiBai,WenkunZhu,RongHe 10.1039/d3en00269a
- [10] An approach to asymmetric synthesis of β-aryl alanines by Pd(0)-catalyzed cross-coupling and cyanate-to-isocyanate rearrangement? Piotr Szcze?niak,Sebastian SteckoRSC Adv., 2015,5, 30882-30888 10.1039/C5RA02818C
Journal Name：Journal of the Chemical Society C: Organic
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)