1341189-52-3Relevant academic research and scientific papers
Nonconcerted cycloaddition of 2H-azirines to acylketenes: A route to N-bridgehead heterocycles
Khlebnikov, Alexander F.,Novikov, Mikhail S.,Pakalnis, Viktoriia V.,Yufit, Dmitry S.
experimental part, p. 9344 - 9352 (2012/01/05)
Reactions of acylketenes, generated from diazo diketones, with 2-unsubstituted and 2-monosubstituted 3-aryl-2H-azirines lead to 1:1 or 2:1 adducts, which are derivatives of 5-oxa-1-azabicyclo[4.1.0]hept-3-ene or 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene. According to DFT B3LYP/6-31G(d) computations, the formation of (4+2)-monoadducts proceeds via a stepwise non-pericyclic mechanism. Reaction with methanol transforms quantitatively both 1:1 and 2:1 adducts into 1,4-oxazepine derivatives.
