Synthesis of phosphorothioates using thiophosphate salts

• Babak Kaboudin and
• Fatemeh Farjadian

Beilstein J. Org. Chem. 2006, 2, No. 4, doi:10.1186/1860-5397-2-4

• route to phosphorothioates via O,O'-dialkyl thiophosphate anion formation. Studies on the reaction of ambident nucleophile ammonium O,O'-diethyl thiophosphate with benzyl halides and tosylate in different solvents show that only S-alkylation is obtained. Reaction of this ambident nucleophile with

• this reagent with benzyl bromide, chloride and tosylate in different aporotic and protic solvents show that S-benzyl O,O'-diethyl phosphorothioate (S-alkylation) was formed as sole product (Scheme 4). We conclude here that changing of leaving group and use of different media gives no O-alkylation

• on the reaction of ambident nucleophile ammonium O,O'-diethyl thiophosphate with benzyl halides and tosylate in different solvents show that only S-alkylation will be obtained as sole product. Reaction of this ambident nucleophile with benzoyl chloride (hard electrophilic center), gave the O