Addition of sulfenyl chlorides to derivatives of ?,?-unsaturated acids and hydrolysis of obtained adducts

Abstract

1. The kinetically controlled addition of alkane (and benzene) sulfenyl chlorides to β-benzalpropionic acid derivatives gave derivatives of β-alkthio-γ-chloro-γ-phenylbutyric acids, which in a moisture-free medium are isomerized to the more stable β-chloro derivatives. 2. The hydrolysis of the C-Cl bond of derivatives of both γ-chloro- and γ-chloro-β(γ)-alkthio-γ-phenylbutyric acids gives β-alkthio-γ-butyrolactones. The hydrolysis proceeds with anchimeric involvement of the sulfur via episulfonium ions. 3. Contrary to the accepted concepts, it is postulated that the addition of sulfenyl chlorides to the derivatives of unsaturated acids and the hydrolysis of the C-Cl bond of the obtained adducts proceed via different intermediates.