Reaction of dithiolactones with benzyne: A novel synthesis of benzo-1,3-dithioles

被引:7
|
作者
Okuma, Kentaro [1 ]
Nojima, Akiko [1 ]
Yokomori, Yoshinobu [2 ]
机构
[1] Fukuoka Univ, Fac Sci, Dept Chem, Jonan Ku, Fukuoka 8140180, Japan
[2] Natl Def Acad, Yokosuka, Kanagawa 2398686, Japan
关键词
benzyne; dithiolactone; benzo-1,3-dithiole; dithiamethylenecyclopropane; 1,2-dithiolane-3-thione;
D O I
10.3987/COM-07-11321
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of benzyne with several kinds of dithiolactones, such as beta-dithiolactone (9), benzothiophene-1-thione (13), 1,2-dithiolane-3-thione (20), and 3,3,5,5-tetramethyl-4-thioxothiolane-2-thione (7), afforded benzo-1,3-dithioles in moderate to good yields, whereas the reaction of benzyne with gamma-thionolactone (16) gave gamma-lactone and diphenyl disulfide.
引用
收藏
页码:1417 / 1424
页数:8
相关论文
共 50 条
  • [41] SYNTHESIS OF 2-(ACYLMETHYL)BENZO-1,3-OXATHIOLES ON BASIS OF ACETYLENE KETONES
    ELOKHINA, VN
    NAKHMANOVICH, AS
    KALIKHMAN, ID
    SOKOLNIKOVA, NP
    VORONKOV, MG
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1975, (10): : 1328 - 1329
  • [42] The synthesis of 2-arylidene or 2-alkylidene-1,3-dithioles by using BU3P-CS2 adduct
    Chen, XD
    Liu, YX
    Cao, RZ
    Xue, M
    Liu, LZ
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1999, 152 : 185 - 190
  • [43] 4,5-dichloro-1,2-dithiole-3-thione in the synthesis of benzimidazole, benzoxazole and benzothiazole derivatives of 1,3-dithioles
    Ogurtsov, VA
    Rakitin, OA
    Rees, CW
    Smolentsev, AA
    MENDELEEV COMMUNICATIONS, 2003, (02) : 50 - 51
  • [44] REACTION OF AMINOAROXYLENE WITH TRIARYLPHOSPHINES .2. SYNTHESIS OF BENZO-1,3,2-OXAPHOSPHOLS
    STEGMANN, HB
    BAUER, G
    SYNTHESIS-STUTTGART, 1973, (03): : 162 - 163
  • [45] THE PREPARATION OF BENZO-1,3-DITHIA-2,4-DIAZINE, A NOVEL ELECTRON-RICH HETEROCYCLE
    KOENIG, H
    OAKLEY, RT
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (02) : 73 - 74
  • [46] Benzo-1,2,3,4-tetrazine 1,3-dioxides: Synthesis and NMR study
    Churakov, AM
    Smirnov, OY
    Ioffe, SL
    Strelenko, YA
    Tartakovsky, VA
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (14) : 2342 - 2349
  • [47] Electrochemical synthesis and crystal structure of copper(I) complex with benzo-1,3-thiozoline-2-thione
    Gu, JS
    Ma, MH
    Shen, LM
    Yu, KB
    ACTA CHIMICA SINICA, 2000, 58 (10) : 1270 - 1274
  • [48] CHEMOSELECTIVE NUCLEOPHILIC RING-OPENING OF GEM DICYANOEPOXIDES - A FACILE SYNTHESIS OF NEW 2-IMINO-4-AMINO-5-CYANO-1,3-DITHIOLES
    GUILLEMET, M
    BAUDYFLOCH, M
    ROBERT, A
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (14) : 906 - 907
  • [49] Synthesis and redox behavior of benzo-1,3-dithiafulvalenes incorporating ferrocene moiety as redox active ligands
    Sarhan, AE
    Izumi, T
    SYNTHETIC METALS, 2004, 140 (01) : 95 - 100
  • [50] SELENIUM HETEROCYCLES .30. SYNTHESIS OF 4-SUBSTITUTED VINYL 2-THIOXO-1,3-DITHIOLES AND 5-SUBSTITUTED VINYL 2-THIOXO-1,3-THIASELENOLES
    SHAFIEE, A
    VOSOOGHI, M
    LALEZARI, I
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (03) : 545 - 547