Monitoring of Grignard Intermediate by MICCS-NMR

Abstract

The Grignard reaction is one of the most famous reactions, and various arguments are done about its reaction mechanism and the structure of the intermediate. However, analysis examples proving with spectral data almost never exist.
We have performed the structural analysis of intermediate of Grignard reaction for aim to resolving the reaction mechanism by MICCS (MIcro Channeled Cell for Synthesis monitoring) -NMR. We succeeded in getting signals of intermediate and in analyzing the structure of intermediate by utilizing ¹H-¹³C correlation two dimensional NMR such as ¹H-¹³C HMBC, and also ¹H-¹H COSY. In addition, we got the structure information of the intermediate by measuring of ESI-MS under the same reaction condition as MICCS-NMR at the same time.