The Use of Bromotrichloromethane in Chlorination Reactions

被引：30
|
作者：
Newman, Stephen G. [1 ]
Bryan, Christopher S. [1 ]
Perez, Didier [1 ]
Lautens, Mark [1 ]
机构：
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
来源：
SYNTHESIS-STUTTGART | 2011年 / 02期
基金：
加拿大自然科学与工程研究理事会;
关键词：
olefination; aldehydes; halogenation; Appel reaction; benzyl halides; STEREOSELECTIVE-SYNTHESIS; TRISUBSTITUTED ALKENES; SELECTIVE SYNTHESIS; VINYL DICHLORIDES; INTERNAL ALKYNES; 1,1-DICHLORO-1-ALKENES; 1,1-DIBROMO-1-ALKENES; KETONES; ALDEHYDES; TRIPHENYLPHOSPHINE;
D O I：
10.1055/s-0030-1258368
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Carbon tetrachloride is no longer used as a common solvent due to its toxicity and harmful environmental impact. The synthesis of gem-dichloroalkenes from aldehydes by using triphenylphosphine typically requires carbon tetrachloride as a solvent. We report that stoichiometric bromotrichloromethane in acetonitrile can be used in place of solvent quantities of carbon tetrachloride in this transformation. Similarly, bromotrichloromethane in dichloromethane can be used for the room-temperature Appel reaction of benzyl alcohols to form benzyl chlorides, which is commonly carried out in refluxing carbon tetrachloride.
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页码：342 / 346
页数：5
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