592489-25-3Relevant academic research and scientific papers
A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate
Kitamura, Mitsuru,Kato, So,Yano, Masakazu,Tashiro, Norifumi,Shiratake, Yuichiro,Sando, Mitsuyoshi,Okauchi, Tatsuo
, p. 4397 - 4406 (2014/06/23)
Organic azides were prepared from primary amines in high yields by a metal free diazo-transfer reaction using 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP), which is safe and stable crystalline. The choice of base was important in the diazo-transfer reaction. In general, 4-(N,N-dimethyl)aminopyridine (DMAP) was efficient, but a stronger base such as alkylamine or DBU was more appropriate for the reaction of nucleophilic primary amines. X-ray single crystal structural analysis and geometry optimization using density functional theory (B3LYP/6-31G**) were conducted to study the ADMP structure, and the diazo-transfer reaction mechanism was explained with the help of the results of these analyses. the Partner Organisations 2014.
Direct synthesis of organic azides from primary amines with 2-azido-1,3-dimethylimidazolinium hexafluorophosphate
Kitamura, Mitsuru,Yano, Masakazu,Tashiro, Norifumi,Miyagawa, Satoshi,Sando, Mitsuyoshi,Okauchi, Tatsuo
experimental part, p. 458 - 462 (2011/03/18)
Organic azides were prepared from primary amines in high yields by metal-free diazo transfer with 2-azido-1,3-dimethylimidazolinium hexafluorophosphate, which is a stable, crystalline solid that is easy to handle. Organic azides were prepared from primary
Synthesis of primary amines and N-methylamines by the electrophilic amination of Grignard reagents with 2-imidazolidinone O-sulfonyloxime
Kitamura, Mitsuru,Chiba, Shunsuke,Narasaka, Koichi
, p. 1063 - 1070 (2007/10/03)
2-Imidazolidinone O-sulfonyloxime reacts with various aryl and alkyl Grignard reagents as an electrophilic amination reagent, giving N-alkylated imines. The resulting imines are transformed to primary amines and N-methyl secondary amines by hydrolysis with CsOH and LiAlH4 reduction, respectively.
