Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides

The electronic effect on the regioselectivity in the alkynylation of phenyloxiranes was investigated using three kinds of metal acetylides. BF3 mediated lithium acetylide provided either the alpha- or beta-alkynylated products by controlling the effect of the para-substituents of the phenyloxiranes. LiClO4 mediated lithium acetylide and titanium acetylide, on the other hand, afforded predominantly the beta- and alpha-products, respectively. (C) 2004 Elsevier Ltd. All rights reserved.