Abstract
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.
Key words
olefination - aldehydes - halogenation - Appel
reaction - benzyl halides
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