Seventeen 1-aryl-2,2-dichloroeyclopropanes were examined by using JR, 13C NMR, and mass spectrometry. The data obtained from IR and Be NMR spectra indicate that the bond strength of carbonchlorine on the cyclopropane ring and the electron density of that carbon depend on the substituent. The mass fragmentation patterns of compounds in this series resemble those of the dibromo analogues. The fragmentation mechanism is proposed to involve the formation of indenium ion through an electrocyclization.
3-Aryl-1,1-dichloro-3-methoxypropenes, methyl 3-aryl-3-methoxypropionates and 3-acetamido-3-aryl-1,1-dichloropropenes are obtained along with N-acetyl-4-aryllactams via anodic oxidation of 1-aryl-2,2-dichlorocyclopropanes in methanol and acetonitrile solutions, respectively.
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