ORGANOLITHIUM REAGENTS FROM ALKYL PHENYL ETHERS

The reaction of primary alkyl or vinyl phenyl ethers (1) as well as 2, 3-dihydrobenzofuran (3) with an excess of lithium powder and a catalyt ic amount of DTBB (5 %) in THF at room temperature leads to the corres ponding organolithium intermediates, which by treatment with different electrophiles [H2O, D2O, Me3SiCl, (BuCHO)-C-t, PhCHO, Me2CO, Et2CO, ( CH2)(4)CO, (CH2)(5)CO, PhCOMe] and final hydrolysis affords the expect ed products 2 and 4. (C) 1998 Elsevier Science Ltd. All rights reserve d.