Selenium and Tellurium Tetrachlorides as Reagents for the Conversion of Alcohols to Alkyl Chlorides and Tellurium Tetrachloride as a Lewis Acid Catalyst for Aromatic Alkylation
作者:Takayoshi Yamauchi、Kaneaki Hattori、Shoichi Mizutaki、Kentaro Tamaki、Sakae Uemura
DOI:10.1246/bcsj.59.3617
日期:1986.11
Selenium tetrachloride(SeCl4) reacts smoothly with alcohols in various nonpolar solvents to give the corresponding alkyl chlorides in 44–97% yield. Similar reaction also proceeds with tellurium tetrachloride (TeCl4), while the treatment of benzyl, 1-phenylethyl, and t-butyl alcohols with TeCl4 in aromatic solvents results in a high yield formation of alkylated aromatics instead of alkyl chlorides.
四氯化硒 (SeCl4) 在各种非极性溶剂中与醇类平稳反应,以 44-97% 的产率生成相应的烷基氯化物。用四氯化碲 (TeCl4) 也能进行类似的反应,而在芳族溶剂中用 TeCl4 处理苄基、1-苯乙基和叔丁醇会导致高产率地生成烷基化芳烃而不是烷基氯。在 SeCl4 的情况下,这种 Friedel-Crafts 芳烃烷基化几乎不会发生。氯化物质不是可能通过 SeCl4 或 TeCl4 离解而放出的氯,而是金属氯化物本身。旋光性 (R)-(+)-1-苯基乙醇向 1-苯基乙基氯的转化几乎完全外消旋。