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Relevant academic research and scientific papers

A method for synthesizing nitroamine compounds

The present invention discloses a method for synthesizing nitroamine compounds, belonging to the field of organic synthesis. The method of the present invention is to a simple and readily available organic compound containing NH structure as the starting material, under the action of nitrogen dioxide free radical precursors, oxidants and reaction gases, stirred in an organic solvent at 40-100 ° C, nitroamine compounds can be obtained. The method of the present invention has the advantages of cheap and easy to obtain raw materials, mild reaction conditions, simple preparation process, good chemical selectivity, wide range of substrate application, easy to amplify, etc., has a large application potential, and lays a good foundation for industrial production.

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids

Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

Synthetic Diversity from a Versatile and Radical Nitrating Reagent

We leverage the slow liberation of nitrogen dioxide from a newly discovered, inexpensive succinimide-derived reagent to allow for the C?H diversification of alkenes and alkynes. Beyond furnishing a library of aryl β-nitroalkenes, this reagent provides unparalleled access to β-nitrohydrins and β-nitroethers. Detailed mechanistic studies strongly suggest that a mesolytic N?N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, electron paramagnetic resonance spectroscopy, we observed direct evidence of a nitryl radical in solution by nitrone spin-trapping. To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C?H partners to prepare isoxazolines and isoxazoles is presented. This approach allows for the formation of an in situ nitrile oxide from a ketone partner, the presence of which is detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeds in a single-operational step using a mild, regioselective, and general protocol with broad chemoselectivity.

Reactions of Secondary Nitramines with Tributyltin Hydride and Tris(trimethylsilyl)silane

The reactions of secondary nitramines (N-nitroamines) with tributyltin hydride or tris(trimethylsilyl)silane have been investigated under free radical conditions.Reactions of nitramines with tributyltin radicals gave mostly the denitration products (secondary amines) whilst reactions with tris(trimethylsilyl)silyl radicals afforded almost exclusively nitrosamines (N-nitrosoamines).

ELECTROPHILIC TETRAALKYLAMMONIUM NITRATE NITRATION. I. CONVENIENT NEW ANHYDROUS NITRONIUM TRIFLATE SYNTHESIS AND IN-SITU HETEROCYCLIC N-NITRATION

Keywords: Anhydrous Nitration, Nitronium Triflate, Tetrabutylammonium Nitrate, Triflic Anhydride Reaction of tetra-n-butylammonium nitrate and triflic anhydride, CF3SO2OSO2CF3 (Tf2O), in dichloromethane (CH2Cl2) solvent at 0 degrees C, produces anhydrous nitronium nitrate, NO2OSO2CF3 (NO2OTf).Subsequent introduction of various heterocycles and their N-acetylated analogs yield N-nitrated products in 20-76 percent yield with an overall one-pot procedure.

Improved Methods for the N-Nitration of Amides

The reactivity of several nitrating mixtures with amides has been compared.Ammonium nitrate/ trifluoroacetic anhydride, morpholinium nitrate/ trifluoroacetic anhydride, and morpholinium nitrate/ heptafluorobutyric anhydride are the reagents of choice sinc

N-NITROSATION AND N-NITRATION OF LACTAMS. FROM MACROLACTAMS TO MACROLACTONES

N-Nitroso and N-nitro derivatives of lactams, from 2-pyrrolidinone to 15-pentadecanelactam, have been characterized by 1H NMR, 13C NMR, and IR spectroscopy.The conversion of these nitrosolactams and nitrolactams to lactones has been systematically (re)investigated.

A Convenient Method For N-Nitration Using Ammonium Nitrate/Trifluoroacetic Anhydride

A mixture of ammonium nitrate and trifluoroacetic anhydride is found to be a convenient reagent for N-nitration in the synthesis of nitramines, nitramides, and nitrimides.Yields are comparable to those from conventional, but less convenient or safe, nitrating reagents.