Alkali Metal 2-(1-Adamantyl)ethynethiolates: Synthesis and Reactions with Electrophilic Reagents

被引：4
|
作者：
Petrov, M. L. [1 ]
Shchipalkin, A. A. [1 ]
Kuznetsov, V. A. [1 ]
Viktorov, B. N. [1 ]
机构：
[1] St Petersburg State Inst Technol, St Petersburg 190013, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 46卷 / 08期
基金：
俄罗斯基础研究基金会;
关键词：
1,2,3-THIADIAZOLES; SULFIDES; ACID; THIOLATE;
D O I：
10.1134/S1070428010080166
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of ethyl 2-[1-(1-admantyl)ethylidene]hydrazine-1-carboxylate with thionyl chloride gave 4-(1-adamantyl)-1,2,3-thiadiazole which readily underwent decomposition by the action of strong bases with formation of alkali metal 2-(1-adamantyl)ethynethiolates. The latter were brought into reactions with proton donors and benzyl halides.
引用
收藏
页码：1214 / 1218
页数：5
相关论文
共 50 条
  • [1] Alkali metal 2-(1-adamantyl)ethynethiolates: Synthesis and reactions with electrophilic reagents
    M. L. Petrov
    A. A. Shchipalkin
    V. A. Kuznetsov
    B. N. Viktorov
    [J]. Russian Journal of Organic Chemistry, 2010, 46 : 1214 - 1218
  • [2] A NEW SYNTHESIS OF 2-(1-ADAMANTYL)THIOPHENE
    LITVINOV, VP
    SHVEDOV, VI
    DERMUGIN, VS
    [J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1982, (08): : 1128 - 1129
  • [3] Improved Synthesis of 2-(1-Adamantyl)-4-bromophenol and 2-(1-Adamantyl)-4-bromoanisole, Intermediates in Adapalene Synthesis
    Sokolenko, V. A.
    Svirskaya, N. M.
    Peterson, I. V.
    Rubailo, A. I.
    [J]. PHARMACEUTICAL CHEMISTRY JOURNAL, 2013, 47 (04) : 217 - 218
  • [4] Improved Synthesis of 2-(1-Adamantyl)-4-bromophenol and 2-(1-Adamantyl)-4-bromoanisole, Intermediates in Adapalene Synthesis
    V. A. Sokolenko*
    N. M. Svirskaya
    I. V. Peterson
    A. I. Rubailo
    [J]. Pharmaceutical Chemistry Journal, 2013, 47 : 217 - 218
  • [5] SYNTHESIS AND REACTIONS OF (1-ADAMANTYL) ACETONE
    STEPANOV, FN
    SIDOROVA, LI
    DOVGAN, NL
    [J]. ZHURNAL ORGANICHESKOI KHIMII, 1972, 8 (09): : 1834 - &
  • [6] Synthesis of 2-(1-adamantyl)imidazo [1,2-a]pyridine and 2-(1-adamantyl)imidazo[1,2-a]pyrimidine derivatives
    Matschay, A
    Skwarski, D
    Sobiak, S
    [J]. POLISH JOURNAL OF CHEMISTRY, 2000, 74 (12) : 1707 - 1712
  • [7] Generation and Reactions of 2-(1-Adamantyl)adamantene. Rearrangement to 3-(1-Adamantyl)-4-protoadamantylidene
    Okazaki, T.
    Isobe, H.
    Kitagawa, T.
    Takeuchi, K.
    [J]. Bulletin of the Chemical Society of Japan, 69 (07):
  • [8] Generation and reactions of 2-(1-adamantyl)adamantene. Rearrangement to 3-(1-adamantyl)-4-protoadamantylidene
    Okazaki, T
    Isobe, H
    Kitagawa, T
    Takeuchi, K
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (07) : 2053 - 2062
  • [9] SYNTHESIS AND SOME REACTIONS OF 1-ADAMANTYL TRIFLUOROMETHANESULFONATE
    TAKEUCHI, K
    MORIYAMA, T
    KINOSHITA, T
    TACHINO, H
    OKAMOTO, K
    [J]. CHEMISTRY LETTERS, 1980, (11) : 1395 - 1398
  • [10] ADAMANTYL-CONTAINING HETEROCYCLES .1. 3-(1-ADAMANTYL)-3-CHLOROPROPENAL IN THE SYNTHESIS OF 2-(1-ADAMANTYL)THIOPHENE AND 5-(1-ADAMANTYL)ISOXAZOLE
    LITVINOV, VP
    DERMUGIN, VS
    SHVEDOV, VI
    BOGDANOV, VS
    [J]. BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1984, 33 (07): : 1451 - 1455
12345