Gem‐dihalocyclopropanes bearing a phenyl group and an additional group were nitrated by using nitric acid in a sulfuric acid matrix. The products from the nitration of aryl rings are major. The presence of a methyl group on the C(2) position of the cyclopropane ring leads to the isoxazoline from nitration at the C(1)‐position instead of that from nitration at the C(2)‐position.
The conformation of trans‐2,11‐dithia‐4e,5,6,7e,8,9‐hexahydro[3.3]paracyclophanes (5, tDTHHPCP) was investigated by using 1H NMR analysis under variable‐temperature condition. Based on the dynamic 1H NMR behavior along with a structure obtained from simulation using the MM2 method, it has been deduced that 5 occurs preferentially in conformer 5a in CD2Cl2 solution, which the two sulfur atoms are situated as the chair form and cyclohexano unit as a distorted boat form. The energy barrier (ΔG‡) for the inversion of the bridge (‐CH2SCH2‐) has been estimated to be 11.6 kcal mol‐1 (600 MHz, Tc = ‐30 °C). The proton chemical shifts are assigned for the individual hydrogen according to the spectra obtained at ‐70 °C.
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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