Phosphonamidothioic acids as thiophosphonylating agents: stereochemistry of reactions of N-tert-butyl-P-phenylphosphonamidothioic acid with alcohols

Authors
Harger, MJP Pater, C
Citation
Mjp. Harger et C. Pater, Phosphonamidothioic acids as thiophosphonylating agents: stereochemistry of reactions of N-tert-butyl-P-phenylphosphonamidothioic acid with alcohols, CHEM COMMUN, (10), 1999, pp. 931-932
Citations number
12
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
10
Year of publication
1999
Pages
931 - 932
Database
ISI
SICI code
1359-7345(19990521):10<931:PAATAS>2.0.ZU;2-5
Abstract
Enantiopure PhP(S)(OH)NHBut reacts with alcohols in CH2Cl2 to give PhP(S)(O H)OR (R = Me, Pr-i, Bu-t); reaction is completely non-stereospecific with ( BuOH)-O-t and largely so with (PrOH)-O-i and very low concentrations of MeO H, pointing to the involvement of a thiometaphosphonate (PhPOS) intermediat e.