85809-26-3Relevant academic research and scientific papers
Reactions with Aziridines, 37. N,N'-Substituted 1,1-Dimethylethylenediamines by Highly Regioselective Ring Opening of Activated 2,2-Dimethylaziridines through Aliphatic Amines
Buchholz, Berthold,Onistschenko, Andreas,Stamm, Helmut
, p. 1311 - 1314 (2007/10/02)
Secondary and primary aliphatic amines 2 form regioselectively N,N'-substituted 1,1-dimethylethylenediamines by reaction with activated 2,2-dimethylaziridines 1.The kind of activation (X in 1), determines the mode of ring opening: X = sulfonyl gives structure 3, X = acyl or 2,4-dinitrophenyl structure 4. - Keywords: 2,2-Dimethylethylenediamines, Activated 2,2-Dimethylaziridine, Nucleophilic Ring Opening, Steric Hindrance, Amines
NUCLEOPHILIC CLEAVAGE OF 2,2-DIMETHYLAZIRIDINES: COMPETITION BETWEEN SN2 AND POSTULATED "SET" MECHANISM.
Stamm, H.,Assithianakis, P.,Buchholz, B.,Weiss, R.
, p. 5021 - 5024 (2007/10/02)
Regioselectivity of nucleophilic attack on 2,2-dimethylaziridines depends on the degree of leaving group activation: in highly activated aziridines it occures at the methylene carbon and in less activated at the tertiary carbon.This latter abnormal ring opening is explained by an SET mechanism.
