Tri-n-butyltin Hydride: A Selective Reducing Agent for 1,3-Dithiolanes

Article abstract of DOI:10.1021/jo01305a004

Tri-n-butyltin hydride has been found to be an effective and selective agent for complete or partial desulfurization of 1,3 dithiolanes 1.The reaction of 1 with 4 equiv of tri-n-butyltin hydride in the presence of 2,2'-azobis(isobutyronitrile) results in complete desulfurization, giving hydrocarbons 2 in good yield, ethane and bis(tri-n-butyltin) sulfide.Two equivalents of hydride specifically cleave the two geminal C-S bonds in 1 to give hydrocarbons 2 and bis(tri-n-butylstannyl) ethanedithiolate.One equivalent of tri-n-butyltin hydride reduces 1 quantitatively to the β-ethyl tri-n-butyltin sulfides 11.