Facile Reduction of Dithiocarbonates Derived from Secondary Alcohols with n-Bu3SnH-Et3B and Synthesis of 2-Furanthiones and 2-Furanones by Intramolecular Addition of Alkoxythiocarbonyl Free Radicals to Acetylenic Linkages

Article abstract of DOI:10.1246/bcsj.63.2578

The reduction of dithiocarbonates or thiocarbonates by n-Bu3SnH-Et3B easily gives the corresponding hydrocarbons.The intermediate alkoxythiocarbonyl radical equivalents are trapped by properly located carbon-carbon multiple bonds.The dithiocarbonates derived from either homopropargylic or homoallylic alcohols produce tetrahydrofuranones upon treatment with n-Bu3SnH-Et3B.Application of this new method to the conversion of carbonyl compounds into olefins is also described.