METALATION OF ARYLMETHYL ALKYL ETHERS

Arylmethyl alkyl ethers 1a-11 were metallated with n-BuLi or sec-BuLi in THF at different temperatures, affording alpha-alkoxy-substituted a rylmethyllithium derivatives. At low temperature, the organometallics derived from methyl and isopropyl ethers are sufficiently stable to re act with added electrophiles affording the expected products 4aa-4jb. On the contrary, under similar conditions, lithium derivatives of prim ary alkyl benzyl ethers rapidly decay to benzyl alcohol 3. (C) 1998 El sevier Science Ltd. All rights reserved.