Development of a Novel Benzyl Mercaptan as a Recyclable Odorless Substitute of Hydrogen Sulfide
作者:Manabu Node、Manabu Matoba、Tetsuya Kajimoto
DOI:10.1055/s-2007-984524
日期:2007.7
odorless substitute of hydrogen sulfide to afford β-mercapto -carbonyl compounds in a Michael addition and to convert alkyl -bromides into alkanethiols. Detrimethoxybenzylation of the -Michael adducts prepared from 4 and α,β-unsaturated esters or -ketones was facilely carried out by treatment with a solvent mixture of trifluoroacetic acid and toluene to give β-mercapto carbonyl compounds. Successive
2,4,6-三甲氧基苄基硫醇 (4) 被开发为硫化氢的无味替代品,以在迈克尔加成中提供 β-巯基-羰基化合物并将烷基溴转化为烷硫醇。通过用三氟乙酸和甲苯的溶剂混合物处理,由 4 和 α,β-不饱和酯或酮制备的 -Michael 加合物的去三甲氧基苄基化很容易进行,得到 β-巯基羰基化合物。作为副产物获得的2,4,6-三甲氧基苄基异硫脲鎓盐的连续碱水解,伴随着二硫化物8以良好收率再生4。二硫化物8也通过用LiAlH 4 还原而转化为4。类似的方案适用于使用烷基溴的 SN 2 反应合成烷硫醇。