- Metal-free synthesis of 1,2-amino alcohols by one-pot olefin aziridination and acid ring-opening
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A one-pot, two-step reaction comprising olefin aziridination and ring-opening of an aziridine intermediate to synthesize 1,2-amino alcohols has been developed. This reaction is suitable for several types of olefin. This methodology allows an efficient and
- Hua, Yong-Gang,Yang, Qian-Qian,Yang, Yi,Wang, Mei-Jing,Chu, Wen-Chao,Bai, Peng-Yan,Cui, De-Yun,Zhang, En,Liu, Hong-Min
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supporting information
p. 2748 - 2751
(2018/06/12)
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- Electrocatalytic aziridination of alkenes mediated by n -Bu4NI: A radical pathway
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Efficient electrocatalytic aziridination of alkenes has been achieved for the first time. A structurally broad range of aziridines was easily accessed using an undivided cell operated at constant current and mediated by a catalytic quantity of n-Bu4
- Chen, Jie,Yan, Wei-Qing,Zeng, Cheng-Chu,Hu, Li-Ming,Lam, Chiu Marco,Little, R. Daniel
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supporting information
p. 986 - 989
(2015/03/18)
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- Sodium-iodoxybenzoate mediated highly chemoselective aziridination of olefins
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Herein we utilized, for the first time, sodium 2-iodoxybenzoate as a highly specific oxidant for PhthNH2 to create a highly chemoselective aziridination reagent. This method efficiently effects aziridination of electron-rich, electron-deficient, allylic alcohol and alkenyl bromide C=C bonds in good to excellent yields. Inter and intramolecular chemoselectivity was demonstrated between electron-rich and electron-deficient alkenes by using this efficient and metal free protocol.
- Bakthavachalam, Ananthan,Chuang, Hui-Chun,Yan, Tu-Hsin
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p. 5884 - 5894
(2015/03/30)
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- Hypoiodite-mediated metal-free catalytic aziridination of alkenes
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Look, no metal: A metal-free catalytic procedure for aziridination of alkenes using tetrabutylammonium iodide as the catalyst, m-chloroperoxybenzoic acid (mCPBA) as the terminal oxidant, and N-aminophthalimide as the nitrenium precursor has been developed (see scheme; right: X-ray structure of one of the products). Control experiments suggests that the active oxidant is in situ generated hypoiodous acid (HIO). Copyright
- Yoshimura, Akira,Middleton, Kyle R.,Zhu, Chenjie,Nemykin, Victor N.,Zhdankin, Viktor V.
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supporting information; experimental part
p. 8059 - 8062
(2012/09/08)
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- Aryl iodide mediated aziridination of alkenes
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(Chemical Equation Presented) Aryl iodide mediated aziridination of a variety of alkenes with N-aminophthalimide under mild conditions (m-CPBA, K 2CO3, CH2Cl2, 25°C) was achieved in moderate to good yields (up to 94%). By recovering the aryl iodide, a recyclable system is developed with product yield over 79% attained for the aziridination of trans-1,2-diphenylethylene.
- Li, Jiayin,Chan, Philip Wai Hong,Che, Chi-Ming
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p. 5801 - 5804
(2007/10/03)
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- Superoxide-mediated synthesis of N-aminoaziridines from N-aminoheterocycles and olefins
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Oxidation of 3-amino-2-methyl-4(3H)-quinazolone and N-aminophthalimide by superoxide ion generated in situ in the presence of olefinic substrates gives rise to the formation of N-aminoaziridine derivatives. Copyright Taylor & Francis, Inc.
- Singh,Singh
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p. 2597 - 2602
(2007/10/03)
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- Aziridination of alkenes with N-substituted hydrazines mediated by iodobenzene diacetate
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Aziridination of a variety of alkenes with N-substituted hydrazines mediated by iodobenzene diacetate under mild conditions (K2CO 3, CH2Cl2) and ambient temperature were achieved in good to excellent yields (up to 99%), and conversions. The practicality and simplicity of this C-N bond formation protocol was exemplified by its application to the aziridination of cholesteryl acetate in a stereoselective manner.
- Li, Jiayin,Liang, Jiang-Lin,Chan, Philip Wai Hong,Che, Chi-Ming
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p. 2685 - 2688
(2007/10/03)
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- Aziridination of Alkenes using 3-Acetoxyaminoquinazolin-4-(3H)ones in the Presence of Tertiary Amines: Evidence for an Azaimide (N-Nitrene) Intermediate
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Solutions of the triethylammonium imide 8, formed from triethylamine and 3-acetoxyaminoquinazolinone 4, react with alkenes at -30 deg C to give aziridines; the reactivity of the aziridinating intermediate is consistent with its formulation as an azaimide (N-nitrene).
- Atkinson, Robert S.,Barker, Emma
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p. 819 - 820
(2007/10/02)
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- Evidence for Phthalimidonitrene as a Common Intermediate in Several Extrusion Reactions
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A common intermediate, presumably phthalimidonitrene 1, is generated in the thermolysis of the aziridinobenzofurans 3 (R = Ac, CO2Me, Bz, COBut and CN) as well as the sulphimide 4, and the azabenzonorbornadiene 5.The transfer of 1 shown in Scheme 1 is zero order in 2-acetylbenzofuran providing further evidence against a concerted bimolecular mechanism 10 for 'nitrene' transfer.
- Atkinson, Robert S.,Jones, David W.,Kelly, Brian J.
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p. 1344 - 1346
(2007/10/02)
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- AZIRIDINATION BY OXIDATIVE ADDITION OF N-AMINOQUINAZOLONES TO ALKENES: EVIDENCE FOR NON-INVOLVEMENT OF N-NITRENES
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Oxidation of 3-aminoquinazolones e.g. (22) with lead tetra-acetate at -20 deg C gives N-acetoxyaminoquinazolones e.g. (23) which are stable in solution at this temperature.These N-acetoxyaminoquinazolones function as inter- and intramolecular aziridinating agents for alkenes and appear to be playing the role previously ascribed to the corresponding N-nitrenes.An analogous N-acetoxyaminophthalimide intermediate (31) is implicated in the lead tetra-acetate oxidation of N-aminophthalimide (4).
- Atkinson, Robert S.,Grimshire, Michael J.,Kelly, Brian J.
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p. 2875 - 2886
(2007/10/02)
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- ADDITION OF PHTHALIMIDONITRENE TO RING-SUBSTITUTED STYRENES
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The addition of phthalimidonitrene to 9-ring-substituted styrenes gives 30-70percent yields of the corresponding previously undescribed 2-aryl-1-phthalimidoaziridines.By the method of competing reactions it was shown that phthalimidonitrene exhibits elect
- Kuznetsov, M. A.,Belov, V. N.
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p. 1611 - 1616
(2007/10/02)
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