Abstract:

As an essential component of fundamental organic chemistry theory, stereoelectronic effects, including the common gauche and anomeric effects, have been intensively investigated and discussed in undergraduate courses. Nevertheless, with the precise prediction and successful synthesis of perfluorocubane, a new cage-type stereoelectronic effect has attracted considerable attention from chemists. Herein, we briefly review the development of stereoelectronic effects, including their wide-ranging applications in organic chemistry. In particular, we highlight recent investigations on perfluorocubane synthesis and discuss the interesting cage-type stereoelectronic effects. The positive interplay between the scientific frontiers and the organic chemistry course will significantly influence the global perspective of students by expanding their knowledge of organic chemistry, and the fundamental concepts and advanced applications of stereoelectronic effects.

Key words: Stereoelectronic effects, Organic synthesis, Perfluorocubane