Tetrahedron

Metalation of arylmethyl alkyl ethers

U Azzena, L Pilo, A Sechi

Index: Azzena, Ugo; Pilo, Luciano; Sechi, Alessandra Tetrahedron, 1998 , vol. 54, # 40 p. 12389 - 12398

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Citation Number: 10

Abstract

Arylmethyl alkyl ethers 1a-11 were metallated with n-BuLi or sec-BuLi in THF at different temperatures, affording α-alkoxy-substituted arylmethyllithium derivatives. At low temperature, the organometallics derived from methyl and isopropyl ethers are sufficiently stable to react with added electrophiles affording the expected products 4aa-4jb. On the contrary, under similar conditions, lithium derivatives of primary alkyl benzyl ethers rapidly ...