721925-99-1Relevant academic research and scientific papers
Rare example of nucleophilic substitution at vinylic carbon with inversion: Mechanism of methyleneaziridine formation by sodium amide induced ring closure revisited
Shiers, Jason J.,Shipman, Michael,Hayes, Jerome F.,Slawin, Alexandra M. Z.
, p. 6868 - 6869 (2007/10/03)
Intramolecular nucleophilic substitution of the C-Br bond of (E)- and (Z)-2-bromobut-2-enylamines by the pendant nitrogen atom leads to 2-ethyleneaziridines by way of stereochemical inversion at the vinylic carbon atom. The stereochemistry of the products is unambiguously established by X-ray crystallography performed on two derivatives. These cyclizations represent some of the first examples of substitution with inversion in unactivated vinylic substrates. In conjunction with additional deuterium-labeling experiments, the accepted mechanism for this reaction is shown to be flawed. Copyright
