Photocatalytic Intramolecular C-H Amination Using N-Oxyureas as Nitrene Precursors
Nitrenes are remarkable high-energy chemical species that enable direct C-N bond formation, typically via controlled reactions of metal-stabilized nitrenes. Here, in contrast, the combined use of photocatalysis with careful engineering of the precursor enabled C-H amination forming imidazolidinones and related nitrogen heterocycles from readily accessible hydroxylamine precursors. Preliminary mechanistic results are consistent with the formation of free carbamoyl triplet nitrenes as reactive intermediates.
Ivanovich, Ryan A.,Polat, Dilan E.,Beauchemin, André M.
supporting information
p. 6360 - 6364
(2020/09/02)
Development of an improved method for conversion of thiuram disulfides into N,N-dialkylcarbamoyl halides and derivatives
A convenient procedure for preparing N,N-disubstituted carbamoyl halides is reported. It consists of two steps: (1) reaction of carbon disulfide and a secondary amine in the presence of a polar organic solvent and oxygen to produce the corresponding tetraalkyl thiuram disulfides and (2) reaction of tetraalkyl thiuram disulfide with a halide in the presence of an aprotic organic solvent to produce the corresponding N,N-disubstituted carbamoyl halide. Copyright Taylor & Francis Group, LLC.
Adeppa,Rupainwar,Misra, Krishna
experimental part
p. 285 - 290
(2011/03/20)
An improved one-pot cost-effective synthesis of N,N-disubstituted carbamoyl halides and derivatives
A convenient one-pot procedure is reported for preparing N,N-disubstituted carbamoyl chlorides by using chlorocarbonylsulfenyl chloride as a carbonylating agent. It comprises the reaction of secondary amines with chlorocarbonylsulfenyl chloride in the presence of an aprotic organic solvent to produce the corresponding N,N-disubstituted carbamoyl halides. Insertion of the carbonyl group without using phosgene is the novelty of this method.
Adeppa,Rupainwar,Misra, Krishna
experimental part
p. 1277 - 1280
(2011/02/23)
Process for the preparation of carbamoyl chlorides derived from secondary amines
Carbamoyl chlorides derived from secondary aliphatic amines having alkyl groups which are branched in the 1-position are prepared by passing phosgene at an elevated temperature into the corresponding, initially taken--if appropriate dissolved in an inert solvent--secondary aliphatic amines having alkyl groups which are branched in the 1-position. The reaction products are intermediates in various specialized fields, particularly in the plant protection sector.
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(2008/06/13)
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