Abstract
An improved method for the generation of dichlorocarbene was developed that utilizes ultrasound in the reaction of carbon tetrachloride with magnesium. High yields of gem-dichlorocyclopropane derivatives can be obtained in the presence of olefins by this method.
Highlights
Gem-dichlorocyclopropanes are valuable intermediates in organic synthesis [1,2]. They are typically prepared by the addition of dichlorocarbene to olefins under phase-transfer catalysis conditions [3,4,5]
Excellent yields of diadducts have been obtained from dienes and dichlorocarbene under ultrasonication and phase-transfer catalyst [9]
We reported a novel route for the generation of dichlorocarbene by the reaction of carbon tetrachloride with magnesium in a neutral medium and hypothesized that the mechanism of these reactions might involve a single electron transfer [10]
Summary
Gem-dichlorocyclopropanes are valuable intermediates in organic synthesis [1,2]. They are typically prepared by the addition of dichlorocarbene to olefins under phase-transfer catalysis conditions [3,4,5]. We reported a novel route for the generation of dichlorocarbene by the reaction of carbon tetrachloride with magnesium in a neutral medium and hypothesized that the mechanism of these reactions might involve a single electron transfer [10]. Sonication is able to effect reactions proceeding through radicals, and ultrasound has provided a distinct alternative to the initiation and enhancement of synthetic reactions involving metals as a reagent [11] This encouraged us to react carbon tetrachloride and magnesium under the new conditions in order to eliminate above drawbacks. Our method is based on the action of ultrasound on carbon tetrachloride and magnesium systems (Scheme 1) Dichlorocarbene formed in this manner adds readily to alkenes, affording excellent yields of corresponding dichlorocyclopropanes.
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