The electronic effect on the regioselectivity in the alkynylation of phenyloxiranes was investigated using three kinds of metal acetylides. BF 3 mediated lithium acetylide provided either the α- or β-alkynylated products by controlling the effect of the para-substituents of the phenyloxiranes. LiClO 4 mediated lithium acetylide and titanium acetylide, on the other hand, afforded predominantly the β- and α-products, respectively.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry