23398-26-7Relevant academic research and scientific papers
The Mechanism of Nucleophilic Substitution of 1-Alkyl-2-(tosyloxymethyl)- aziridines
D'hooghe, Matthias,De Kimpe, Norbert
, p. 271 - 274 (2004)
The stereochemical course of nucleophilic substitution of 1-alkyl-2-(tosyloxymethyl)aziridines has been elucidated by a study using a chiral substrate, which confirmed that no initial ring opening and subsequent ring closure occurred but that instead direct substitution at the exocyclic methylene function took place. Consequently, these N-alkylaziridines exhibit a totally different reactivity towards nucleophiles as compared to the corresponding activated aziridines with an electron-withdrawing group at nitrogen, which has important stereochemical implications.
