AN EXTREMELY EFFICIENT SYNTHESIS OF THIOPHENE 1,1-DIOXIDES - OXIDATION OF THIOPHENE DERIVATIVES WITH DIMETHYLDIOXIRANE

被引：41
|
作者：
MIYAHARA, Y
INAZU, T
机构：
[1] Department of Chemistry, Faculty of Science, Kyushu University 33 Hakozaki, Higashi-ku, Fukuoka
来源：
TETRAHEDRON LETTERS | 1990年 / 31卷 / 41期
关键词：
D O I：
10.1016/S0040-4039(00)98003-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Dimethyldioxirane was found to oxidize electron-rich thiophene derivatives, including sterically hindered thiophenophanes, to the corresponding thiophene 1,1-dioxides in excellent yields. Electronwithdrawing groups on a thiophene ring substantially retarded the oxidation, but dimethyldioxitane remained superior to other reagents. © 1990.
引用
收藏
页码：5955 / 5958
页数：4
相关论文
共 50 条
  • [41] Thiophene 1, 1-dioxides as unique building blocks in modern organic synthesis and materials chemistry
    Department of Chemistry, M V Lomonosov Moscow State University, Leninskie Gory, 119992 Moscow, Russia
    Russ. Chem. Rev., 2006, 12 (1015-1048):
  • [42] Synthesis and anti-tubercular activity of 3-substituted benzo[b]thiophene-1,1-dioxides
    Chandrasekera, N. Susantha
    Bailey, Mai A.
    Files, Megan
    Alling, Torey
    Florio, Stephanie K.
    Ollinger, Juliane
    Odingo, Joshua O.
    Parish, Tanya
    PEERJ, 2014, 2
  • [43] Electrochemically-promoted synthesis of benzo[b]thiophene-1,1-dioxides via strained quaternary spirocyclization
    Li, Ruitao
    Yuan, Dafu
    Ping, Mengqi
    Zhu, Yuyi
    Ni, Shaofei
    Li, Ming
    Wen, Lirong
    Zhang, Lin-Bao
    CHEMICAL SCIENCE, 2022, 13 (34) : 9940 - 9946
  • [44] THIADIAZIRIDINE 1,1-DIOXIDES - SYNTHESIS AND CHEMISTRY
    TIMBERLAKE, JW
    ALENDER, J
    GARNER, AW
    HODGES, ML
    OZMERAL, C
    SZILAGYI, S
    JACOBUS, JO
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (10): : 2082 - 2089
  • [45] Synthesis and structure of bromonitrothiolene 1,1-dioxides
    Efremova, IE
    Abzianidze, VV
    Swenson, D
    Bartak, D
    Berestovitskaya, VM
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2003, 73 (04) : 646 - 651
  • [46] Synthesis and Structure of Bromonitrothiolene 1,1-Dioxides
    I. E. Efremova
    V. V. Abzianidze
    D. Swenson
    D. Bartak
    V. M. Berestovitskaya
    Russian Journal of General Chemistry, 2003, 73 : 646 - 651
  • [47] First synthesis of selenophene 1,1-dioxides
    Nakayama, J
    Matsui, T
    Sugihara, Y
    Ishii, A
    Kumakura, S
    CHEMISTRY LETTERS, 1996, (04) : 269 - 270
  • [48] A STEREOSELECTIVE SYNTHESIS OF DIALKYLAMINOMETHYL SUBSTITUTED HALOBUTADIENES VIA AMINE INDUCED RING-OPENING OF THIOPHENE-1,1-DIOXIDES
    GRONOWITZ, S
    HALLBERG, A
    NIKITIDIS, G
    TETRAHEDRON, 1987, 43 (21) : 4793 - 4802
  • [49] BENZOTHIAZETE 1,1-DIOXIDES
    AO, MS
    BURGESS, EM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (20) : 5298 - &
  • [50] MASS SPECTROSCOPIC FRAGMENTATION REACTIONS .34. FRAGMENTATION BEHAVIOR OF ALKYLATED THIOPHENE-1,1-DIOXIDES
    BUDZIKIEWICZ, H
    LANGE, D
    ORGANIC MASS SPECTROMETRY, 1992, 27 (04): : 489 - 494
12345