Abstract:

The most favored anti-conformation of ethane would turn into gauche-conformation when the vicinal hydrogen atoms are replaced by two fluorine atoms. Such a switch shows how the gauche effect impacts the relative conformation of organic molecules. Herein, we briefly survey the history of the gauche effect as well as its broad applications in organic synthesis. Particularly, we highlight the recent investigations on the related sulfur-fluorine gauche effect. With the aid of experiments, we confirmed that the sulfur-fluorine gauche effect could be easily regulated via the subtle change of positive charges on the sulfur atom. Such a positive interplay between scientific research and organic course teaching would profoundly help students to understand the basic concepts and advanced applications of the sulfur-fluorine gauche effect.

Key words: Gauche effect, Stereoelectronic effect, Conformation