Aryl 1-chloroalkyl sulfoxides as acyl anion equivalents: a new synthesis of vinyl sulfides, ketones, and diketones from aryl 1-chloroalkyl sulfoxides and α,ω-dichloro-α,ω-disulfinylalkanes
作者:Tsuyoshi Satoh、Daisaku Taguchi、Chihiro Suzuki、Satoshi Fujisawa
DOI:10.1016/s0040-4020(00)01015-2
日期:2001.1
anhydride and NaI in acetone at low temperature afforded vinyl sulfides in high yields. The vinyl sulfides were converted to ketones by hydrolysis with HClO4 in refluxing 1,4-dioxane in good yields. In this procedure, the lithiated aryl 1-chloroalkyl sulfoxides acted as acyl anion equivalents. The procedure was extended to a synthesis of α,ω-diketones starting from α,ω-dichloro-α,ω-disulfinylalkanes. The procedure
在低温下用三氟乙酸酐和NaI处理由芳基1-氯烷基亚砜通过与碘代烷烃的烷基化反应而合成的芳基α-氯烷基亚砜,可以高产率得到乙烯基硫化物。在回流的1,4-二恶烷中,通过用HClO 4水解,将乙烯基硫化物转化为酮。在该程序中,锂化的芳基1-氯烷基亚砜起酰基阴离子当量的作用。该程序扩展到从α,ω-二氯-α,ω-二亚磺酰基烷烃开始合成α,ω-二酮。当α,ω-二亚磺酰基烷烃的碳链长度大于四个时,发现该方法行之有效,并且发现二酮的收率有些变化(60-80%)。