Electrochemically induced transformation of 4-halomethyl-4-methylcyclohexa-2,5-dien-1-ones into 3,4-dimethylphenol

被引：3
|
作者：
Gavrilova, G. V. [1 ]
Moiseeva, A. A. [1 ]
Beloglazkina, E. K. [1 ]
Gavrilov, A. A. [1 ]
Zyk, N. V. [1 ]
机构：
[1] Moscow MV Lomonosov State Univ, Fac Chem, Moscow 119992, Russia
来源：
RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2009年 / 79卷 / 02期
关键词：
Glassy Carbon Electrode; Electrochemical Reduction; Cyclic Voltammetry Curve; Halogen Atom; Diethyl Malonate;
D O I：
10.1134/S1070363209020169
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Electrochemical behavior of 4-halomethyl-4-methylcyclohexa-2,5-dien-1-ones and 2,6-dibromo-4,4-dimethylcyclohexa-2,5-dien-1-one was studied. Reductive dehalogenation of cyclohexa-2,5-dien-1-ones having a halogen atom at the neopentyl-like carbon atom gives the corresponding carbanion which undergoes anionic cyclopropyl-allyl rearrangement with subsequent addition of proton to form 3,4-dimethylphenol.
引用
收藏
页码：264 / 268
页数：5
相关论文
共 50 条
  • [1] Electrochemically induced transformation of 4-halomethyl-4-methylcyclohexa-2,5-dien-1-ones into 3,4-dimethylphenol
    G. V. Gavrilova
    A. A. Moiseeva
    E. K. Beloglazkina
    A. A. Gavrilov
    N. V. Zyk
    Russian Journal of General Chemistry, 2009, 79 : 264 - 268
  • [2] Bromination of 4-Dichloromethyl-4-methylcyclohexa-2,5-dien-1-ones
    Gavrilova, G. V.
    Rusetskaya, I. N.
    Gavrilov, A. A.
    Trushkov, I. V.
    Krut'ko, D. P.
    SYNTHETIC COMMUNICATIONS, 2007, 37 (16) : 2729 - 2736
  • [3] Electrochemically induced transformation of 4(6)-dihalomethyl-4(6)-methylcyclohexa-2,5(2,4)-dien-1-ones into 4(2)-methyltropones
    Moiseeva, A. A.
    Gavrilova, G. V.
    Beloglazkina, E. K.
    Krut'ko, D. M.
    Zyk, N. V.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2011, 81 (08) : 1658 - 1663
  • [4] Electrochemically induced transformation of 4(6)-dihalomethyl-4(6)-methylcyclohexa-2,5(2,4)-dien-1-ones into 4(2)-methyltropones
    A. A. Moiseeva
    G. V. Gavrilova
    E. K. Beloglazkina
    D. M. Krut’ko
    N. V. Zyk
    Russian Journal of General Chemistry, 2011, 81 : 1658 - 1663
  • [5] EVIDENCE FOR HOMOALLYLIC STABILIZATION OF CARBANIONS . REACTIONS OF PHOSPHINES WITH 4-TRIHALOMETHYLCYCLOHEXA-2,5-DIEN-1-ONES
    MILLER, B
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (03) : 751 - &
  • [6] 4-substituted 4-hydroxycyclohexa-2,5-dien-1-ones with selective activities against colon and renal cancer cell lines
    Wells, G
    Berry, JM
    Bradshaw, TD
    Burger, AM
    Seaton, A
    Wang, B
    Westwell, AD
    Stevens, MFG
    JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (04) : 532 - 541
  • [7] THE NITRATION OF 4-METHYLPHENOL, 3,4-DIMETHYLPHENOL AND 3,4,5-TRIMETHYLPHENOL WITH NITROGEN-DIOXIDE
    HARTSHORN, MP
    JUDD, MC
    VANNOORT, RW
    WRIGHT, GJ
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (05) : 689 - 697
  • [8] Reactions of Phosphorylated 2,6-Di-tert-butyl-4-methylidenecyclohexa-2,5-dien-1-ones with Aliphatic, Aromatic, and Heteroaromatic Thiols
    Gazizov, M. B.
    Pistsova, A. L.
    Ismagilov, R. K.
    Shamsutdinova, L. P.
    Karimova, R. F.
    Burangulova, R. N.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (05) : 1101 - 1103
  • [9] Reactions of phosphorylated 2,6-di-tert-butyl-4-methylidenecyclohexa-2,5-dien-1-ones with aliphatic, aromatic, and heteroaromatic thiols
    M. B. Gazizov
    A. L. Pistsova
    R. K. Ismagilov
    L. P. Shamsutdinova
    R. F. Karimova
    R. N. Burangulova
    Russian Journal of General Chemistry, 2017, 87 : 1101 - 1103
  • [10] SYNTHESIS OF 3-ETHYL-4-METHYLPHENOL AND 3-ISOPROPYL-4-METHYLPHENOL FROM 3,4-DIMETHYLPHENOL VIA TRICHLOROMETHYL INTERMEDIATES
    NEWMAN, MS
    BAYERLEIN, F
    JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (10): : 2804 - &
12345