85809-15-0Relevant academic research and scientific papers
Reactions with Aziridines, 41. - Highly Regioselective (Abnormal) Ring Opening of 1-Benzoyl-2,2-dimethylaziridine by Simple Nitrile Anions
Assithianakis, Petros,Stamm, Helmut
, p. 855 - 858 (2007/10/02)
The anions 3a-e of the acetonitriles 2a-e cleave the aziridine ring of 1-benzoyl-2,2-dimethylaziridine (1) at the tertiary C-atom (abnormal opening) and provide in this way good yields of the 4-(benzoylamino)-3,3-dimethylbutyronitriles 5a-e and of the 2-(benzoylimino)pyrrolidine 7a, respectively.Positional isomers could not be detected.
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.
