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首页> 外文期刊>RSC Advances >Breaking bonds with electrons: stepwise and concerted reductive cleavage of C-S, C-Se and Se-CN bonds in phenacylthiocyanates and phenacylselenocyanates
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Breaking bonds with electrons: stepwise and concerted reductive cleavage of C-S, C-Se and Se-CN bonds in phenacylthiocyanates and phenacylselenocyanates

机译：用电子打破粘合：在苯酰硫氰酸酯和苯酰基硒氰酸酯中的C-S，C-SE和SE-CN键合的逐步和齐齐异的还原切割

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摘要

The mechanistic aspects of the electrochemical reduction of phenacylthio- and selenocyanates have been studied. With phenacylthiocyanates (1), a change in the reductive cleavage mechanism is observed as a function of the substituent on the phenyl ring. While a stepwise mechanism involving the intermediacy of a radical anion is followed for substrates bearing a strong electron withdrawing group, such as cyano and nitro substituent (1d, 1e), and a concerted mechanism is favoured for compounds bearing an electron-donating or no substituent on the phenyl ring (1a-c). A regioselective bond cleavage leads to the fragmentation of the CH2-S bond with all compounds 1a-e, further yielding the corresponding 1,4-diketone (3) as products. Contrastingly, with phenacylselenocyanates (2), two different reductive cleavages occur involving the breaking of both the CH2-Se and Se-CN bonds. Several products are obtained, all coming from nucleophilic attack at the alpha (phenacyl) carbon or the selenium atom.
机译：研究了苯十六酮和硒氰酸酯的电化学减少的机械方面。对于苯基硫氰酸酯（1），将在苯环上的取代基的函数中观察到还原切割机制的变化。虽然涉及基团阴离子的中间体的逐步机制被伴随着具有强电子抽出基团的基板，例如氰基和硝基取代基（1d，1e），并且符合机构对携带电子提供的或没有取代基的化合物在苯环（1A-C）上。区域选择性粘合性裂解导致CH2-S键与所有化合物1A-E的破碎，进一步产生相应的1,4-二酮（3）作为产物。比较地，用苯基硒硅氧烷酯（2），发生两种不同的还原性裂解，涉及分解CH2-SE和SE-CN键。获得了几种产品，所有产品都来自α（苯酰基）碳或硒原子的亲核攻击。

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  • 来源
    《RSC Advances》 |2015年第16期|共8页
  • 作者

    Bouchet Lydia M.; Penenory Alicia B.; Robert Marc; Argueello Juan E.;

  • 作者单位

    Univ Nacl Cordoba Fac Ciencias Quim Dept Quim Organ INFIQC CONICET UNC RA-5000 Cordoba Argentina;

    Univ Nacl Cordoba Fac Ciencias Quim Dept Quim Organ INFIQC CONICET UNC RA-5000 Cordoba Argentina;

    Univ Paris Diderot Sorbonne Paris Cite CNRS Lab Electrochimie Mol Unit Mixte Rech Univ F-75205 Paris 13 France;

    Univ Nacl Cordoba Fac Ciencias Quim Dept Quim Organ INFIQC CONICET UNC RA-5000 Cordoba Argentina;

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