59564-67-9Relevant academic research and scientific papers
Aziridines, 61 +"--"+ Ring Opening of 2,2-Dimethyl-1-sulfonylaziridines by Anilines: Regioselectivity and Revised Structure of Main Products
Buchholz, Berthold,Lin, Pen-Yuan,Onistschenko, Andreas,Stamm, Helmut
, p. 483 - 487 (2007/10/02)
It is shown (1) that in the most reactions of anilines 2 with 1-sulfonyl-2,2-dimethylaziridines 1 both isomeric products 3 and 4 are formed, (2) that the "normal" product 4 obtained by attack on position 3 of 1 usually arises in a small or negligible amount that seems to decrease with decreasing basicity of 2, and (3) that the amount of 4 strongly increases with increasing steric demand of 2.Formation of 4 is explained by a lag of bond making in SN2. +"--"+ N-Aryl-N'-sulfonyl-gem-dimethylethylenediamines, 1-Sulfonyl-2,2-dimethylaziridines, Regioselectivity of Nucleophilic Ring Opening, Steric Hindrance Effect, Basicity Effect
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.
