Synthesis and some properties of O-acyl-and O-nitrophenylhydroxylamines

Tamura, Y.; Minamikawa, Jun‐ichi; Sumoto, Kunihiro; Fujii, Shoji; Ikeda, Masazumi

doi:10.1021/jo00946a045

Cited by 172 publications

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“…Arguably, currently the most direct synthesis of NH--sulfoximines involves NH transfer to sulfoxides (Scheme 1, a). Methods to achieve this have involved harsh and explosive or unstable reagents such as azides, 15 O--mesitylenesulfonylhydroxylamine (MSH) or O--(2,4--dinitrophenyl)--hydroxylamine (DPH), 16 and technological advances have been exploited to facilitate use of these reagents. 17 Richards reported the use of DPH with Rh catalysts for the direct preparation of NH--sulfoximines from sulfoxides under mild conditions.…”

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Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

et al. 2017

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Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

et al. 2017

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“…Consequently, there are very few examples of unprotected electrophilic NH sources, which would be more desirable as it avoids the requirement for additional steps and improves atom economy. Activated reagents such as O ‐mesitylenesulfonylhydroxylamine (MSH) or O ‐(2,4‐dinitrophenyl)‐hydroxylamine (DPH) have been employed but these suffer from instability and the required additional steps for their preparation 2, 3. In an important recent example of NH transfer, Falck, Kurti, and co‐workers reported a direct synthesis of unprotected (i.e.…”

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Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides

et al. 2016

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A new system for NH transfer is developed for the preparation of sulfoximines, which are emerging as valuable motifs for drug discovery. The protocol employs readily available sources of nitrogen without the requirement for either preactivation or for metal catalysts. Mixing ammonium salts with diacetoxyiodobenzene directly converts sulfoxides into sulfoximines. This report describes the first example of using of ammonia sources with diacetoxyiodobenzene to generate an electrophilic nitrogen center. Control and mechanistic studies suggest a short‐lived electrophilic intermediate, which is likely to be PhINH or PhIN+.

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“…Decomposition points (onset) were recorded on a differential scanning calorimeter-thermal gravimetric instrument (TGA/DSC1, METTLER TOLEDO LF/1100). The thermal stabilities of DABNT were determined by differential scanning calorimetry (DSC) and thermogravimetry (TGA) at heating rates of 5 K·min [10] and O-tosylhydroxylamine (THA) [31,32] were synthesized according to literature methods.…”

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A Facile Synthesis of 3,3'-Dinitro-5,5'-Diamino-Bi-1,2,4-Triazole and Its Thermal Decomposition Study

Ma¹,

Lu²,

Qu³

et al. 2017

Cent. Eur. J. Energ. Mater.

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3,3'-Dinitro-5,5'-diamino-bi-1,2,4-triazole (DABNT) was synthesized by a facile method and its crystalline density was determined as 1.839 g·cm −3 at 293(2) K by X-ray diffraction. Its thermal decomposition kinetics and mechanism were studied by means of differential scanning calorimetry-thermogravimetry (DCS-TG), in situ thermolysis by rapid-scan Fourier transform infrared spectroscopy (RSFTIR) and simultaneous TG-IR technology. The results showed that the apparent activation energies obtained by the Kissinger, Ozawa and Starink methods were 122.9 kJ·mol , 118.4 kJ·mol −1 and 138.7 kJ·mol −1 , respectively. The decomposition reaction process of DABNT starts with the transformation from a primary amine to a secondary amine and then the loss of one nitro-group from the DABNT structure. Gaseous products, such as N2O and H2O, were detected from decomposition in the range of 50-300 °C. Density functional theory (DFT) calculations were further employed to illustrate the decomposition mechanism. The above-mentioned information on the synthesis and thermal behaviour is quite useful for the scale-up and evaluation of the thermal safety of DABNT.

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Synthesis and some properties of O-acyl-and O-nitrophenylhydroxylamines

Cited by 172 publications

References 0 publications

Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides

A Facile Synthesis of 3,3'-Dinitro-5,5'-Diamino-Bi-1,2,4-Triazole and Its Thermal Decomposition Study

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