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Synthesis, characterization and electrochemistry of diferrocenyl-1,3-thiazoles, 1,3-oxathiolanes, benzo-[b]-1,4-oxathiepines and ethyl 2-propenethioates
Journal of Organometallic Chemistry ( IF 2.1 ) Pub Date : 2020-06-15 , DOI: 10.1016/j.jorganchem.2020.121363
Elena I. Klimova , Carlos Guerrero Rubio , Jesús García-Valdés , Eder Nuñez-Cruz , Elena Martínez-Klimova , Irina P. Beletskaya , Marcos Flores-Álamo , Jessica J. Sánchez García

2,3-Diferrocenylcyclopropenium salts react with bis-1,4-N,S- and bis-1,4-O,S-nucleophiles to yield: (1′,2′-diferrocenylvinyl)-1,3-thiazoles 6-8; (1′,2′-diferrocenylvinyl)-1,3-oxathiolanes 12a,b, 14a,b, 15b; 2,3-diferrocenyl-4H-1,4-benzo-[b]-oxathiepines 13a,b; ethyl2,3-diferrocenyl-2-propenethioates 16a,b and 2,3-diferrocenyl-3-methylthioacryl carbaldehydes Z/E-5b. New reactions for the synthesis of diferrocenyl heterocycles and diferrocenyl-2-propenethioates with several heteroatoms N,S, O and O,S, in molecules were found. The characterization of the new compounds was conducted by IR, 1H, 13C NMR spectroscopy, elemental analysis, and X-ray analysis of the compounds E-5b, 6 and 12b. The redox properties of the cycles 6, 8, 12a,b, 14a,b were investigated using cyclic (CV), differential pulse (DPV), and square wave (SWV) voltammetries. All compounds showed two reversible mono electronic oxidation processes since ΔEp(I) and ΔEp(II) are close to 0.060 V. Furthermore, the ΔE1/2 are enough separated to conclude that all the tested compounds have partially delocalized electronic charge in the mixed-valence state, according to the Robin-Day classification.



中文翻译:

二铁茂铁基-1,3-噻唑,1,3-氧杂硫杂环戊烷,苯并[ b ] -1,4-氧杂吡啶和2-丙硫基乙基乙酯的合成,表征和电化学

2,3-Diferrocenylcyclopropenium盐与之反应-1,4- Ñ小号-和-1,4- ö小号-nucleophiles以产生:(1',2'- diferrocenylvinyl)-1,3-噻唑6 - 8;(1',2'-二茂铁基乙烯基)-1,3-氧杂硫杂环戊烷12ab14ab15b ; 2,3-二茂铁基-4 H -1,4-苯并-[ b ]-氧杂吡啶类13ab ; 2,3-二茂铁基-2-丙硫基乙基酯16a,b和2,3-二茂铁基-3-甲基硫代丙烯酸丙烯醛Z/ E - 5b。发现了分子中具有几个杂原子NSOOS的二铁茂铁杂环和二铁茂铁-2-丙硫醇酯的合成新反应。通过化合物E - 5b612b的IR,1 H,13 C NMR光谱,元素分析和X射线分析进行新化合物的表征。该循环的氧化还原性质6812Ab14a的b使用环状(CV),差分脉冲(DPV),和方波(SWV)伏安法研究。由于ΔEp(I)和ΔEp(II)接近0.060 V,所有化合物均表现出两个可逆的单电子氧化过程。此外,ΔE1 /2足够分离,可以得出结论,所有测试化合物在混合气体中均具有部分离域电子电荷价状态,根据Robin-Robin-Day分类。

更新日期:2020-07-13
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