Conjugate Additions of Secondary Amines and Water to Allenyl Perfluoroalkyl Sulfones

Abstract

Abstract Preparation of allenyl perfluoroalkyl sulfones from perfluoroalkyl sulfinyl chlorides and their reactions with secondary amines and water were studied. At room temperature secondary amines reacted readily with allenyl perfluoroalkyl sulfones to give the corresponding enamine adducts, which underwent rearrangement to afford conjugate enamines in refluxing toluene. Good diastereoslectivities were observed in the addition of diethylamine to γ ‐ethyl‐ γ ‐methylallenyl perfluoroalkyl sulfones. In refluxing acetonitrile, water could also undergo the similar addition with allenyl perfluoroalkyl sulfones.