此反应是Hunsdiecker反应反应的改进法。羧酸在四乙酸铅和氯化锂作用下加热脱羧氯代得到氯化烷烃的反应。反应中四乙酸铅和氯化锂反应生成氯气,直接进行反应。
反应机理
和Hunsdiecker反应反应类似,也是自由基机理。
反应操作
Cyclobutyl chloride (2). To a solution of cyclobutanecarboxylic acid 1 (100 mg, 10 mmol) in PhH (10 mL) was added Pb(OAc)4 (2 g, 4.5 equiv) and the mixture was stirred at 20 ℃ until it became homogeneous. Anh LiCl (240.4 mg, 6.2 mmol) was added under N2 and the mixture was heated at 81 ℃. Workup afforded 90.5 mg of 2 (100%).
【Kochi JK, J Org Chem., 1965, 30, 3265】
相关文献
1 Kochi JK J Org Chem 1965 30 3265
2R Kochi JK Org React 1972 19 326
3 Grob CA Synthesis 1973 493
4 Roy S Steroids 1982 39 537
5 Kapustina NI Russ Chem Bull Int 2004 53 2200
编译自:Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 263-264.