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.

引用

页码：342 / 346

页数：5

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