- Versatile new reagent for nitrosation under mild conditions
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Here we report a new chemical reagent for transnitrosation under mild experimental conditions. This new reagent is stable to air and moisture across a broad range of temperatures and is effective for transnitrosation in multiple solvents. Compared with traditional nitrosation methods, our reagent shows high functional group tolerance for substrates that are susceptible to oxidation or reversible transnitrosation. Several challenging nitroso compounds are accessed here for the first time, including 15N isotopologues. X-ray data confirm that two rotational isomers of the reagent are configurationally stable at room temperature, although only one isomer is effective for transnitrosation. Computational analysis describes the energetics of rotamer interconversion, including interesting geometry-dependent hybridization effects.
- Galloway, Jordan D.,Sarabia, Cristian,Fettinger, James C.,Hratchian, Hrant P.,Baxter, Ryan D.
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supporting information
p. 3253 - 3258
(2021/05/06)
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- NITROSATION REAGENTS AND METHODS
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Provided are compounds that can find use as nitrosation reagents. Provided are nitrosation methods that include reacting a substrate with one of the provided nitrosation reagents and thereby generating a nitrosation product. Provided are kits including a nitrosation reagent. Provided are compositions wherein the nitrosation reagent is enriched in the 15N isotope.
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Paragraph 00158; 00182; 00183; 00202-00205; 00230-00233; ...
(2022/02/06)
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- Bismuth chloride-sodium nitrite: A novel reagent for chemoselective N-nitrosation
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Bismuth(III) chloride-sodium nitrite was used as a mild and efficient reagent for N-nitrosation of various tetrazoles, secondary amines, and amides under ambient conditions. Nitrosation took place chemoselectively at the nitrogen atom, giving corresponding N-nitroso derivatives in good to excellent yield. Copyright Taylor & Francis Group, LLC.
- Chaskar, Atul C.,Langi, Bhushan P.,Deorukhkar, Amol,Deokar, Hrushikesh
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experimental part
p. 604 - 612
(2009/07/04)
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- Tin(IV) chloride-sodium nitrite as a new nitrosating agent for N-nitrosation of amines, amides and ureas under mild and heterogeneous conditions
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We have developed a new method of N-nitrosation of various secondary and tertiary amines, amides and ureas using a mixture of tin(IV) chloride and sodium nitrate. This method leads to a selective, high-yielding and mild heterogeneous N-nitrosation by in situ generation of nitrosyl chloride (NOCl). The reaction can be carried out in several different solvents such as chloroform, dichloromethane, ethers, ethyl acetate and alcohols, at room temperature. Georg Thieme Verlag Stuttgart.
- Celaries, Benoit,Parkanyi, Cyril
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p. 2371 - 2375
(2008/02/03)
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- N-NITROSATION AND N-NITRATION OF LACTAMS. FROM MACROLACTAMS TO MACROLACTONES
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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.
- Torra, Nuria,Urpi, Felix,Vilarrasa, Jaume
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p. 863 - 868
(2007/10/02)
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