抄録
The reaction of cyclopropanol silyl ethers with diethylaminosulfur trifluoride in dichloromethane usually causes ring opening to produce allylic fluorides. However, cyclopropyl silyl ethers bearing a strong electron-donating substituent at C1 or an electron-withdrawing substituent at C2 do not afford allylic fluorides but fluorocyclopropanes. It has also been proved that an electron-donating substituent at C2 of the cyclopropanol silyl ethers promotes ring opening in the reaction with diethylaminosulfur trifluoride. These reactions proceed through allyl cations or cyclopropyl cations derived from cyclopropyl silyl ethers. In the cases of the reaction of cyclopropanol silyl ethers with diethylaminosulfur trifluoride in electron rich aromatic compounds, the carbocations derived from cyclopropyl silyl ethers mainly reacted with aromatic compounds.
