Syntheses and fluoride-ion-mediated hydrolysis of phosphoroselenoic acid ester and amides
β Scribed by Toshiaki Murai; Shinsuke Inaji; Tohru Takenaka
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- English
- Weight
- 149 KB
- Volume
- 20
- Category
- Article
- ISSN
- 1042-7163
- DOI
- 10.1002/hc.20544
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β¦ Synopsis
Phosphoroselenoic acid ester and amides containing binaphthoxy moiety were prepared by reacting phosphoroselenoyl chloride with alcohols and secondary amines. The resulting amides underwent fluoride-ion-mediated hydrolysis with a THF solution of tetrabutylammonium fluoride to give two types of phosphoroselenoic acid ammonium salts: one with a fluorine atom and another with a binaphthoxy group on the phosphorus atom. The ratio of these products depended on the substituents on the nitrogen atom of the amides. A similar reaction of the ester with tetrabutylammonium fluoride gave two types of ammonium salts. The formation of these products was confirmed by converting them to the corresponding methyl esters.
π SIMILAR VOLUMES
Lanthanide ion-induced hydrolyses of methyl esters, ethyl esters, and amides of a-amino acids were systematically studied. In the hydrolysis of the alkyl esters, all the lanthanide ions are effective and the catalytic activities decrease in the order Ce(III), Nd(III) b Sm(III) b Eu(III) b Gd(III), C