121846-92-2Relevant academic research and scientific papers
Reactions with Aziridines, 51. - Ring Opening of cis-2-Benzyl-3-phenyl-1-(phenylsulfonyl)aziridine by Alkoxide. The First Eliminative Fission of an Aziridine with Uncharged Nitrogen
Stamm, Helmut,Speth, Dieter
, p. 1795 - 1798 (2007/10/02)
The title compound 2 can be ring-opened in three ways by alcoholic sodium alkoxide; nucleophilic substitutive opening in (the benzylic) position3 and in position 2 as well as the novel nucleophilic eliminative opening which is initiated by deprotonation of the benzylic substituent .The primary cleavage product 5 of attack (c) is an allylic sulfonamide that slowly isomerizes to give the elusive enamide 6, the precursor of the isolated ketone 7.Attack (a) predominates with methoxide and less so with ethoxide.Attack (c) increases with size (and basicity?) of the alkoxide and is the only detected reaction with tert-butoxide. - Key Words: Aziridines, regioselectivity of ring opening/ Allylamide-enamide isomerization/ Benzenesulfonamide, N-(1,3-diphenylallyl)
