Unknown

Dataset Information

0

Synthesis of phosphorothioates using thiophosphate salts.


ABSTRACT: Reactions of O,O'-dialkyl thiophosphoric acids with alkyl halides, in the presence of a base, provide a direct synthetic 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 benzoyl chloride (a hard electrophile), gave the O-acylation product. A simple, efficient, and general method has been developed for the synthesis of phosphorothioates through a one-pot reaction of alkyl halides with the mixture of diethyl phosphite in the presence of triethylamine/sulfur/and acidic alumina under solvent-free conditions using microwave irradiation.

SUBMITTER: Kaboudin B 

PROVIDER: S-EPMC1421414 | biostudies-literature | 2006 Mar

REPOSITORIES: biostudies-literature

altmetric image

Publications

Synthesis of phosphorothioates using thiophosphate salts.

Kaboudin Babak B   Farjadian Fatemeh F  

Beilstein journal of organic chemistry 20060316


Reactions of O,O'-dialkyl thiophosphoric acids with alkyl halides, in the presence of a base, provide a direct synthetic 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 benzoyl chloride (a hard electrophile), gave the O-acylation product. A simple, e  ...[more]

Similar Datasets

| S-EPMC8650099 | biostudies-literature
| S-EPMC9405834 | biostudies-literature
| S-EPMC4316994 | biostudies-literature
| S-EPMC3701385 | biostudies-literature
| S-EPMC9004633 | biostudies-literature
| S-EPMC11372555 | biostudies-literature
| S-EPMC8697689 | biostudies-literature
| S-EPMC8456962 | biostudies-literature
| S-EPMC10870718 | biostudies-literature
| S-EPMC9034104 | biostudies-literature