5-(2-Thienylsulfanyl)thiophene-2-carbaldehyde: Thioacetalization, chloromethylation, and oxidation

被引：3
|
作者：
Papernaya, L. K. [1 ]
Levanova, E. P. [1 ]
Klyba, L. V. [1 ]
Albanov, A. I. [1 ]
机构：
[1] Russian Acad Sci, Favorskii Irkutsk Inst Chem, Siberian Div, Irkutsk 664033, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 45卷 / 07期
关键词：
DERIVATIVES;
D O I：
10.1134/S1070428009070094
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
5-(2-Thienylsulfanyl)thiophene-2-carbaldehyde reacted with propane-1-thiol and propane-1,3-dithiol in the presence of chloro(trimethyl)silane to give previously unknown 5-[bis(propylsulfanyl)methyl]-2-(2-thienylsulfanyl)thiophene and 2-[5-(2-thienylsulfanyl)thiophen-2-yl]-1,3-dithiane. Chloromethylation of 5-(2-thienylsulfanyl)thiophene-2-carbaldehyde with formaldehyde in a stream of hydrogen chloride in the presence of zinc chloride resulted in the formation of an oligomeric product consisting of thiophene rings connected alternately by sulfur and methylene bridges. The oligomer is formed via fast polycondensation of the primary chloromethylation product with the initial aldehyde. 5-(2-Thienylsulfanyl)thiophene-2-carbaldehyde was oxidized at the sulfide and aldehyde groups with 30% hydrogen peroxide in glacial acetic to produce 5-(2-thienylsulfonyl)thiophene-2-carboxylic acid.
引用
收藏
页码：1036 / 1039
页数：4
相关论文
共 50 条
  • [1] 5-(2-Thienylsulfanyl)thiophene-2-carbaldehyde: Thioacetalization, chloromethylation, and oxidation
    L. K. Papernaya
    E. P. Levanova
    L. V. Klyba
    A. I. Albanov
    Russian Journal of Organic Chemistry, 2009, 45 : 1036 - 1039
  • [2] 5-(fluoren-9-ylidenemethyl)thiophene-2-carbaldehyde
    Perasinova, Lucia
    Stefko, Martin
    Vegh, Daniel
    Kozisek, Jozef
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O3972 - O3973
  • [3] 5-[(2-Hydroxyethyl)(methyl)amino]thiophene-2-carbaldehyde
    Sun, Xian-Shun
    Shao, Nan-Qi
    Li, Dan -Dan
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 : O724 - +
  • [4] Thiophene-2-carbaldehyde azine
    Geiger, David K.
    Geiger, H. Cristina
    Szczesniak, Laura M.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O916 - +
  • [5] Benzo[b]thiophene-2-carbaldehyde
    Mancuso, Raffaella
    Gabriele, Bartolo
    MOLBANK, 2014, (02)
  • [6] 5-{[(E)-2-(4-Iodophenyl)hydrazinylidene]methyl}thiophene-2-carbaldehyde
    Wardell, Solange M. S. V.
    de Lima, Geraldo M.
    Tiekink, Edward R. T.
    Wardell, James L.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O271 - U1616
  • [7] CONFORMATIONAL PREFERENCE IN THIOPHENE-2-CARBALDEHYDE
    SALMAN, SR
    ORGANIC MAGNETIC RESONANCE, 1982, 20 (03): : 151 - 153
  • [8] Thiophene-2-carbaldehyde 2,4-dinitrophenylhydrazone
    Yin, Zhi-gang
    Qian, Heng-yu
    Li, He-ping
    Hu, Jie
    Zhang, Chun-xia
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O2421 - U3136
  • [9] Crystal structure of 5-[bis(4-ethoxy-phenyl)amino]thiophene-2-carbaldehyde
    Tan, Jing-Yun
    Kong, Ming
    Wu, Jie-Ying
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 : O1075 - +
  • [10] Thiophene-2-carbaldehyde 3-nitrophenylhydrazone
    Wardell, James L.
    Low, John N.
    Glidewell, Christopher
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O1848 - O1850
12345