Formation of Cyclopropanes and Epoxides from Vinylselenonium Salts

Article abstract of DOI:10.1246/bcsj.66.2042

Treatment of vinyl- and (5-oxo-1-cyclopentenyl)sulenonium tetrafluoroborates 2 and 4 with a variety of carboanions gives cyclopropane derivatives 3 and 5 in good yields.The reaction of vinylselenonium salt 2 with sodium alkoxides in the presence of aldehydes gives various kinds of glycidyl ethers 7 in excellent yields.The reaction of 2 with hydroxyacetone in the presence of K2CO3 affords cyclized products 8 and 9 together with the Michael addition product 10.