23054-66-2Relevant articles and documents
Regioselectivity in Nucleophilic Ring Opening of 2-Methylaziridines. Lag of Bond Making as Model for the Abnormal Opening
Lin, Pen-Yuan,Bentz, Gunther,Stamm, Helmut
, p. 23 - 34 (1993)
The regioselectivity ratio RS=normal:abnormal opening of activated 2-methylaziridines 2 by nucleophiles is found to range from 0.10 to unmeasurable large (only normal opening=substitution at CH2 by strongly basic carbanions).RS is assumed to result from SN2 variants differing in the degree to which bond breaking is ahead of bond making including perhaps synchronous SN2.Bond breaking will be more ahead for the N-CMe bond.High nucleophilic power pushes bond making toward a synchronous process resulting in great RS.The decrease in RS with acyl activation relative to sulfonyl activation is in accord with a flattening of the nitrogen pyramid (planarization effect).The planarization effect is retained in acidic medium by O-protonation: RS 0.10-0.14 for methanolysis as compared to RS 0.43 for N-protonated sulfonylaziridine 2h.AM1 calculations support the planarization hypothesis. - No indication for SET with trityl anion was found.
N-Acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides: Highly selective and efficient reagents for acylation of amines in water
Ebrahimi, Sara,Saiadi, Safoura,Dakhilpour, Simin,Mirsattari, Seyed Nezamoddin,Massah, Ahmad Reza
, p. 95 - 104 (2016/04/26)
A variety of N-acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides (1a-e) were synthesized in one pot from 4-chloroaniline under solvent-free conditions and have been developed as chemoselective N-acylation reagents. Selective protection of primary amines in the presence of secondary amines, acylation of aliphatic amines in the presence of aryl amines, and monofunctionalization of primary-secondary diamines as well as selective N-acylation of amino alcohols using these reagents are described. All of the acylation reactions were carried out in water as a green solvent. High stability and easy preparation of these acylating reagents are other advantages of this method.
A novel, facile route to β-fluoroamines by hydrofluorination using superacid HF-SbF5
Thibaudeau, Sebastien,Martin-Mingot, Agnes,Jouannetaud, Marie-Paule,Karam, Omar,Zunino, Fabien
, p. 3198 - 3200 (2008/02/13)
A range of unsaturated amines and sulfonamides were converted to β-fluoro nitrogen analogues after hydrofluorination in superacid HF-SbF5, based on the formation of highly reactive electrophilic intermediates. The Royal Society of Chemistry.
