Convenient synthesis of allylic thioethers from phosphorothioate esters and alcohols.
The synthesis of allylic thioethers arising from the reaction between phosphorothioate esters and alcohols is described. The synthesis is accomplished in one step by the addition of an exogenous alkoxide to the corresponding allylic phosphorothioate ester. It is demonstrated that this process is amenable to various functional groups and a wide variety of heterocycles. In contrast to conventional methods for thioether synthesis, no malodorous sulfur compounds such as thioacetic acid or thiols are required.
Robertson
Forest
F
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.
Wu
Jimmy
J
D000438:Alcohols / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D009946:Organothiophosphorus Compounds / Q000737:chemistry*; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
D000438:Alcohols; D000498:Allyl Compounds; D004952:Esters; D009946:Organothiophosphorus Compounds; D013440:Sulfides