THE REACTION BETWEEN THIOPHOSGENE AND TRIALKYL PHOSPHITES
- 1 October 1988
- journal article
- research article
- Published by Taylor & Francis in Phosphorus and Sulfur and the Related Elements
- Vol. 40 (1-2) , 1-8
- https://doi.org/10.1080/03086648808072886
Abstract
The reaction between trialkyl phosphites and thiophosgene, even at low temperature, does not lead to esters of thiocarbonyl bisphosphonic acid as had previously been reported. The initial products appear to be stabilised phosphorus ylids formed by two carbophilic and one thiophilic reactions between thiophosgene and the trialkyl phosphite with no desulfuration. Following thermal or acidic treatment, the ylids undergo protonation-dealkylation reactions to give phosphorothio-substituted methane bisphosphonates.Keywords
This publication has 12 references indexed in Scilit:
- PPi analogs as inhibitors of human T-lymphotropic virus type III reverse transcriptaseAntimicrobial Agents and Chemotherapy, 1986
- Trapping of carbanionic species synthesis of new salt-free ylids and phosphoranesTetrahedron Letters, 1980
- Structural studies of carbanionic species formed from phosphonates: anions of diethyl benzyl- and cyanomethylphosphonatesThe Journal of Organic Chemistry, 1978
- Chemistry of thiono- and selenonophosphoranes. A mechanistic study of chlorination reactions of phosphorus thionoesters >P(S)OR: reactive intermediates and stereochemistryJournal of the American Chemical Society, 1978
- Syntheses of [(1-alkylthio)]- and (1-mercapto)cycloalkane phosphonic esters by the reactions of cycloalkanethiones with trialkyl phosphitesThe Journal of Organic Chemistry, 1978
- Korrektur: Zur Struktur der „Methan‐tris‐phosphorylderivate”︁Journal für Praktische Chemie, 1972
- Generation of phosphite ylides from trithiocarbonates and trimethyl phosphite and their application to the extension of carbon chainsTetrahedron Letters, 1967
- Fluorothiocarbonyl Compounds. II.1 Reactions of HexafluorothioacetoneThe Journal of Organic Chemistry, 1965
- Stereospecific Syntheses of Olefins from 1,2-Thionocarbonates and 1,2-Trithiocarbonates. trans-CyclohepteneJournal of the American Chemical Society, 1965
- A New, Stereospecific Olefin Synthesis from 1,2-DiolsJournal of the American Chemical Society, 1963