Crotyl chloride
Crotyl chloride is an organochloride with the molecular formula or. It is a derivative of 2-butene with a chlorine atom at a terminal carbon. It exhibits cis-trans isomerism about the double bond; the (E) isomer predominates in commercial preparations.
Preparation
It can be produced by the chlorination of crotyl alcohol by chlorinating agents such as triphenylphosphine dichloride.Applications
Treatment of crotyl halides with magnesium produces crotyl Grignard reagents. The chloride is more stable than the bromide. These reagents can then be used in the Grignard reaction for crotylation of carbonyl compounds.Dehydrohalogenation of crotyl chloride was once used as a laboratory route to produce butadiene, though the pyrolysis of cyclohexene is preferred according to Organic Syntheses. Crotyl chloride may be used as a model compound for other allylic hydrochlorocarbons.