Molecular Addition Compounds. 17. Borane and Chloroborane Adducts with Organic Sulfides for Hydroboration
作者:Marek Zaidlewicz、Josyula V. B. Kanth、Herbert C. Brown
DOI:10.1021/jo0009090
日期:2000.10.1
distillation. Consequently, diisoamyl sulfide is a new promising borane carrier. Bis(2-methoxyethyl) sulfide, easily synthesized from the low cost thiodiethanol, is three times more soluble in water than 1,4-oxathiane. Its borane adduct is 6.0 M in BH3 and can substitute for more expensive borane-1,4-oxathiane in hydroboration reactions. Applications of these new borane adducts in the synthesis of mono- and dichloroborane
与二甲基硫醚和1,4-氧杂蒽相比,已检查了以下硫化物作为硼烷载体:叔丁基甲基硫醚,异戊基甲基硫醚,乙基异戊基硫醚,叔丁基异戊基硫醚,二异戊基硫醚,四氢噻吩,四氢噻喃,硫代苯甲醚,3-乙基硫代四氢呋喃,双(3-四氢呋喃基)硫化物和双(2-甲氧基乙基)硫化物。它们对硼烷的络合能力按以下顺序增加:硫代茴香醚<醚硫化物<二烷基硫化物<二甲基硫化物。硫化物的硼烷加合物是高于0摄氏度的液体。硫代苯甲醚加合物在室温下失去乙硼烷。加合物对1-辛烯的反应性按硫化物络合能力的相反顺序增加。二异戊基硫醚具有温和的,空灵的,令人愉快的香气,它的合成是经济的,硼烷加合物(BH3中的4.2 M)在室温下可长时间稳定。硫化物可以通过蒸馏从氢硼化-氧化产物中回收。因此,二异戊基硫醚是一种新兴的硼烷载体。由低成本的硫代二乙醇容易合成的双(2-甲氧基乙基)硫化物在水中的溶解度是1,4-氧杂蒽的三倍。它的硼烷加合物在BH3中为6