Oxidative removal of 1,3-dithiane protecting groups by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ)
作者:Kiyoshi Tanemura、Hiroshi Dohya、Masanori Imamura、Tsuneo Suzuki、Takaaki Horaguchi
DOI:10.1039/p19960000453
日期:——
carbonyl compounds in good yields by treatment with 1.5 equiv. of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in MeCN–H2O (9:1). The reactions of 2-aryl-substituted 1,3-dithianes bearing electron-donating groups on the benzene ring with DDQ afforded thioesters along with aldehydes. 1,3-Dithiolanes derived from aromatic aldehydes were transformed to thioesters, whereas 1,3-dithiolanes derived from aliphatic
通过用1.5当量处理,已将许多1,3-二硫杂环丁烷以良好的产率有效地转化为母体羰基化合物。MeCN–H 2中2,3-二氯-5,6-二氰基对苯醌(DDQ)的分析O(9:1)。苯环上带有给电子基团的2-芳基取代的1,3-二硫烷与DDQ的反应提供了硫酯和醛。衍生自芳族醛的1,3-二硫杂环戊烷被转化为硫酯,而衍生自脂族和芳族酮的1,3-二硫杂环戊烷在这些反应条件下稳定。二苯基二硫缩醛是稳定的,除了4-甲氧基-和3,4-二甲氧基-苯甲醛二苯基二硫缩醛可以得到相应的醛。已经研究了在1,3-二硫杂环戊烷或二苯基二硫缩醛存在下的1,3-二噻吩的选择性裂解反应。