Why Do the Chiral Shift Groups Keep Their Configuration in the Nucleophilic 1,2-Rearrangements
XU Jia-Xi1**, MA Yuan2
1. College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China; 2. Department of Chemistry, Tsinghua University, Beijing 100084, China
Abstract Nucleophilic 1,2-rearrangements are one class of important organic reactions. Leaving of the leaving groups and shift of the shift groups can be either stepwise or concerted. However, the rearrangements always occur with retention of the configuration at the migrating carbon of the shift groups. This article introduces using hyperconjugation and stereoelectronic effect to explain the phenomenon and to grasp the general rule, hoping to provide help for teachers' teaching and students' understanding in teaching and learning organic chemistry.
XU Jia-Xi, MA Yuan. Why Do the Chiral Shift Groups Keep Their Configuration in the Nucleophilic 1,2-Rearrangements[J]. Chinese Journal of Chemical Education, 2022, 43(24): 115-119.