4,5-dichloro-4',5'-ethylenedioxytetrathiafulvalene | 289504-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶英
• 英文名称: 4,5-dichloro-4',5'-ethylenedioxytetrathiafulvalene
• 英文别名: 2-(4,5-Dichloro-1,3-dithiol-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dioxine
• CAS: 289504-25-2
• 化学式: C₈H₄Cl₂O₂S₄
• 分子量: 331.289
• InChiKey: GHLPHQWXOOXFJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-dichloro-4',5'-ethylenedioxytetrathiafulvalene 在 tert-butylammonium hexafluorophosphate(V) 作用下， 以 1,1,2-三氯乙烷 为溶剂， 生成
  参考文献：
  名称：

  Syntheses, Structure and Conducting Properties of Halogenated Ethylenedioxytetrathiafulvalenes

  摘要：

  4,5-Diiodo-, 4,5-dibromo-, and 4,5-dichloro-4',5'-ethylenedioxytetra-thiafulvalenes (EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2) were synthesized in moderate to good yields by the two routes. The first route contains the reaction of EDO-TTF with LDA, followed by quenching with halogenated reagents, and the second route consists of the P(OR)(3)-mediated cross-coupling of 4,5-dihalogenated 1,3-dithiole-2-ones with 4,5-ethylenedioxy-1,3-dithiole-2-thione. The structures of EDO-TTFI2 and EDO-TTFCl2 were determined by X-Ray analysis. The radical-cation salts derived from EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2 show high conductivities, although these compounds contain electron-withdrawing halogens as the substituent.

  DOI：

  10.3987/com-00-s(i)79
• 作为产物：
  描述：

  2,3-bis(dimethyldithiocarbamyl)-1,4-dioxane 在 sodium hydrogensulfide 、 正丁基锂 、 溴 、 二异丙胺 、 lithium bromide 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醇 、 正己烷 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， -78.0~150.0 ℃ 、2.0 kPa 条件下， 反应 31.45h， 生成 4,5-dichloro-4',5'-ethylenedioxytetrathiafulvalene
  参考文献：
  名称：

  Syntheses, Structure and Conducting Properties of Halogenated Ethylenedioxytetrathiafulvalenes

  摘要：

  4,5-Diiodo-, 4,5-dibromo-, and 4,5-dichloro-4',5'-ethylenedioxytetra-thiafulvalenes (EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2) were synthesized in moderate to good yields by the two routes. The first route contains the reaction of EDO-TTF with LDA, followed by quenching with halogenated reagents, and the second route consists of the P(OR)(3)-mediated cross-coupling of 4,5-dihalogenated 1,3-dithiole-2-ones with 4,5-ethylenedioxy-1,3-dithiole-2-thione. The structures of EDO-TTFI2 and EDO-TTFCl2 were determined by X-Ray analysis. The radical-cation salts derived from EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2 show high conductivities, although these compounds contain electron-withdrawing halogens as the substituent.

  DOI：

  10.3987/com-00-s(i)79

文献信息

• Radical-Cation Salts Based on Brominated and Chlorinated Ethylenedioxytetrathiafulvalenes
  作者：Masahiko Iyoda、Eiji Ogura、Takahiro Takano、Kenji Hara、Yoshiyuki Kuwatani、Takehiro Kato、Naoki Yoneyama、Jun-ichi Nishijo、Akira Miyazaki、Toshiaki Enoki

  DOI：10.1246/cl.2000.680

  日期：2000.6

  Radical-cation salts derived from 4,5-dibromo-4′,5′-ethylenedioxy- and 4,5-dichloro-4′,5′-ethylenedioxytetrathiafulvalenes (EDO-TTFBr2 and EDO-TTFCl2) showed metallic conductivities in spite of their electron-withdrawing substituents.

  尽管具有吸电子取代基，但由4,5-二溴-4′,5′-乙烯二氧基和4,5-二氯-4′,5′-乙烯二氧基四硫富瓦烯（EDO-TTFBr2和EDO-TTFCl2）衍生的自由基盐仍表现出金属导电性。