A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.
Molecules. 2021 Jun 18;26(12):3729. doi: 10.3390/molecules26123729.
The regioselective synthesis of novel functionalized condensed organochalcogen compounds by chalcogenocyclofunctionalization reactions based on chalcogen halides and the natural products thymol and carvacrol has been developed. The reactions of selenium dibromide with allyl thymol and allyl carvacrol proceeded in methylene chloride at room temperature in the presence of NaHCO affording bis[(7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] and bis[(4-isopropyl-7-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] selenides in 90-92% yield. Similar sulfides were obtained in 70-72% yields by the reaction of sulfur dichloride in chloroform under reflux. Trihalotellanes containing the same organic moieties were synthesized from allyl thymol, allyl carvacrol and tellurium tetrachloride or tetrabromide in quantitative yields. Corresponding functionalized ditellurides were prepared in 91-92% yields by the reduction of the trichlorotellanes with sodium metabisulfite in two-phase solvent system. The comparison of reactivity of sulfur, selenium and tellurium halides in chalcogenocyclofunctionalization and distinguishing features of each reaction were discussed.
新型功能化稠合有机硫化合物的区域选择性合成 通过基于卤代硫和天然产物百里酚和香芹酚的硫环官能化反应 已经开发出来。二溴化硒与烯丙基百里酚和烯丙基香芹酚在室温下在碳酸氢钠存在下在二氯甲烷中反应，以 90-92%的产率得到双[(7-异丙基-4-甲基-2,3-二氢-1-苯并呋喃-2-基)甲基]和双[(4-异丙基-7-甲基-2,3-二氢-1-苯并呋喃-2-基)甲基]硒醚。类似的硫醚通过回流氯仿中二氯化硫的反应以 70-72%的产率获得。含有相同有机部分的三卤代碲烷从烯丙基百里酚、烯丙基香芹酚和四氯化碲或四溴化碲以定量产率合成。用亚硫酸钠在两相溶剂体系中还原三氯化碲烷，以 91-92%的产率制备相应的功能化二碲化物。讨论了卤代硫、硒和碲在硫环官能化中的反应性比较以及每个反应的区别特征。
