Addition of Dichlorocarbene to alkenes to give dichlorocyclopropanes
Description: Alkenes treated with chloroform (CHCl3) and strong base will form dichlorocarbenes, which add to alkenes to form cyclopropanes.
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Real-Life Examples:
Org. Synth. 1976, 55, 12
DOI Link: 10.15227/orgsyn.055.0012
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Org. Synth. 1969, 49, 35
DOI Link: 10.15227/orgsyn.049.0035
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Org. Synth. 1961, 41, 76
DOI Link: 10.15227/orgsyn.041.0076
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I think the stereo chemistry is wrong here. They don’t always add syn as Dichlorocarbene rxn’s are sterospecfic cis.
Syn addition and “cis” addition essentially mean the same thing.