Cyclofunctionalization of Hydroxyolefins Induced by Arenetellurinyl Acetate

Article abstract of DOI:10.1021/jo00279a030

Treatment of arenetellurinic anhydride (1) with acetic acid or anhydride readily formed arenetellurinyl acetate (2).It underwent not only oxytellurinylation of an olefin but also intramolecular cyclofunctionalization of various hydroxyolefins to cyclic ethers.The latter reaction was effectively accelerated by addition of boron trifluoride etherate or tin(IV) chloride and highly regio- and stereoselective.The tellurium functional group introduced in the cyclic ethers could be manipulated into other versatile groups by telluroxide elimination, halogenolysis, and reductive detelluration.