Metalation of arylmethyl alkyl ethers

被引：11
|
作者：
Azzena, U [1 ]
Pilo, L [1 ]
Sechi, A [1 ]
机构：
[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
来源：
TETRAHEDRON | 1998年 / 54卷 / 40期
关键词：
lithium and compounds; metalation; elimination reactions; rearrangements;
D O I：
10.1016/S0040-4020(98)00758-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Arylmethyl alkyl ethers 1a-11 were metallated with n-BuLi or sec-BuLi in THF at different temperatures, affording alpha-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 decay to benzyl alcohol 3. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码：12389 / 12398
页数：10
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