A Mild Synthesis of Vinyl Halides and gem-Dihalides Using Triphenyl Phosphite−Halogen-Based Reagents
摘要:
A new application of (PhO)(3)P-halogen-based reagents to the synthesis of vinyl halides and gem-dihalides is described. Vinyl halides were prepared in good to excellent yields from enolizable ketones, whereas aldehydes afforded the corresponding gem-dihalides. The halogenation proceeded smoothly under mild conditions.
Reaction of E- and Z-4-chlorohept-3-enes (RZCl and RECl with lithium gives reduction products in addition to the organolithium compound. This reduction occurs with partial inversion of the doublebond while retention of configuration takes place when the n-butyllithium exchange reaction is used.