Thermal rearrangements of allylic sulfinates to sulfones: A mechanistic study

CHED 329

David B. Ball and Lisa S. Hernandez, dball@csuchico.edu. Department of Chemistry, California State University, Chico, Chico, CA 95929-0210
Allylic sulfinates have been postulated to thermally rearrange to allylic sulfones by either an electrocyclic process or one that involves allylic carbocations. Using appropriate deuterium labeling, the substrate structure relationship of the mechanism of these rearrangements is elucidated.