An example of a stepwise mechanism for the catalyst-free 1,3-dipolar cycloaddition between a nitrile oxide and an electron rich alkene

作者：Siadati Seyyed Amir^*

来源：Tetrahedron Letters, 2015, 56(34): 4857-4863.

DOI：10.1016/j.tetlet.2015.06.048

• Stepwise
• 1,3-Dipolar cycloaddition
• Reaction pathways
• Mechanism

The present Letter studies possible pathways for the non-catalyzed 1,3-dipolar cycloaddition (1,3-DC) reaction between a nitrite oxide derivative and a highly electron-rich alkene. A diagram of the free energy surface during the reaction coordinate was prepared by considering all routes of the 1,3-DC reaction between methyl nitrile oxide and tetraamino ethylene and by detecting any possible species which could form in the course of the predicted pathways. The results indicated that the stepwise pathway was preferable in comparison with the concerted route. Therefore, it was concluded that a switching of the mechanism from concerted to stepwise was the outcome when using strong electron donor functional groups on the dipolarophile.

• 出版日期2015-8-19