Nucleophilic Additions to Alkylidene Bis (sulfoxides)—Stereoelectronic Effects in Vinyl Sulfoxides

T Wedel, T Gehring, J Podlech, E Kordel…

Index: Wedel, Tobias; Gehring, Timo; Podlech, Joachim; Kordel, Elena; Bihlmeier, Angela; Klopper, Wim Chemistry - A European Journal, 2008 , vol. 14, # 15 p. 4631 - 4639

Full Text: HTML

Citation Number: 23

Abstract

Abstract Conjugate additions of nucleophiles (eg enolates, amines and malonate anions) to bis (p-tolylsulfinyl) alkenes, alkylidene-1, 3-dithiane-1, 3-dioxides and alkylidene-1, 3- dithiolane-1, 3-dioxides have recently been published. Reasons for different selectivities and reaction rates will be discussed by consideration of steric and electronic effects. The preferred mode of attack can be explained by stereoelectronic effects (hyperconjugation) ...