Direct observation of the unstable intermediates in radical addition reaction by using an interfacing microchip combined with an NMR.

Direct observation of the unstable intermediate in the radical addition reaction of the oxime ether 1 mediated by triethylborane (Et(3)B) is described using (1)H and (11)B micro channeled cell for synthesis monitoring (MICCS), which was recently developed as an interfacing microchip for NMR. It was possible that the signal of the intermediate was observed as a result of using MICCS technique with a standard NMR instrument. This result supports the structure of the intermediate analyzed by diffusion-ordered spectroscopy (DOSY) NMR method in a previous paper. The procedure of micro channeled cell for synthesis monitoring-nuclear magnetic resonance (MICCS-NMR) was much easier than that of DOSY method. It was proven that it could be applied to the reaction in an anhydrous condition.