Tin(II) chloride catalyzed reactions of diazodiphenylmethane with vicinal diols in an aprotic solvent. The reactions with cis- and trans-1,2-cyclohexanediols and 1,2-propanediol
作者:Sigthor Petursson
DOI:10.1016/s0008-6215(03)00039-9
日期:2003.4
Conditions where catalyst destruction is negligible show that the rate of the reaction with the trans-isomer is larger than with the cis-isomer. The reactions with 1,2-propanediol show small difference between the selectivity for the primary and secondary hydroxyl groups. This is in contrast with the tin(II) chloride catalyzed reactions of diazomethane and diazophenylmethane in methanol with carbohydrates
该论文报道了重氮二苯基甲烷与顺式和反式1,2-环己二醇以及R,S-1,2-丙二醇在1,2-二甲氧基乙烷中的氯化锡(II)催化反应,并鉴定了形成的单二苯基甲基醚。已表明该催化剂可用于顺式和反式环己二醇,但该催化剂在高试剂浓度下不稳定,特别是在反式异构体的情况下。催化剂破坏可忽略不计的条件表明与反式异构体的反应速率大于与顺式异构体的反应速率。与1,2-丙二醇的反应表明伯羟基和仲羟基的选择性之间的差异很小。这与甲醇中重氮甲烷和重氮苯基甲烷与碳水化合物,甘油和核糖核苷的氯化锡(II)催化反应形成对比,