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.
引用
收藏
页码：12389 / 12398
页数：10
相关论文
共 24 条
  • [1] AZZENA U, 1995, TETRAHEDRON LETT, V36, P5641
  • [2] SINGLE AND DOUBLE REDUCTIVE CLEAVAGE OF C-O BONDS OF AROMATIC DIMETHYL ACETALS AND KETALS - GENERATION OF BENZYLIC MONOCARBANIONS AND DICARBANIONS
    AZZENA, U
    MELLONI, G
    PISANO, L
    SECHI, B
    [J]. TETRAHEDRON LETTERS, 1994, 35 (36) : 6759 - 6762
  • [3] Benzyl delta-chlorobutil ether - A new unsymmetrical derivative of tetramethylene glycol
    Bennett, GM
    Hock, AL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1927, : 472 - 476
  • [4] ELABORATION OF ALPHA-SUBSTITUTED BENZYL ALKYL ETHERS AND SULFIDES BY SUPPRESSION OF THE WITTIG AND RELATED REARRANGEMENTS VIA COMPLEXATION TO TRICARBONYLCHROMIUM
    BLAGG, J
    DAVIES, SG
    HOLMAN, NJ
    LAUGHTON, CA
    MOBBS, BE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (09): : 1581 - 1589
  • [5] COWTON ELM, 1996, J CHEM SOC CHEM COMM, P839
  • [6] Gualtieri F, 1996, SYNLETT, P447
  • [7] HOFFMANN RW, 1992, LIEBIGS ANN CHEM, P725
  • [8] KATRITZKY AR, 1987, SYNTHESIS-STUTTGART, P415
  • [9] CONVERSION OF LACTONES INTO ETHERS
    KRAUS, GA
    FRAZIER, KA
    ROTH, BD
    TASCHNER, MJ
    NEUENSCHWANDER, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (11) : 2417 - 2419
  • [10] alpha-methoxy-benzylmetals: Original synthesis and reactivity
    Krief, A
    Bousbaa, J
    [J]. TETRAHEDRON LETTERS, 1997, 38 (35) : 6289 - 6290
123