REACTION OF DIALKOXYTHIOXAPHOSPHORANESULFENYL CHLORIDES WITH DIALKYL TRIMETHYLSILYL PHOSPHITES. NEW STEREOSELECTIVE ROUTE TO THE UNSYMMETRICAL TETRAALKYL DITHIOPYROPHOSPHATES. PREPARATION OF DIASTEREOISOMERIC 2-TRIMETHYLSILYLOXY-4-METHYL-1,3,2-DIOXAPHOSPHORINANES
- 1 July 1986
- journal article
- research article
- Published by Taylor & Francis in Phosphorus and Sulfur and the Related Elements
- Vol. 28 (3) , 299-305
- https://doi.org/10.1080/03086648608072821
Abstract
Unsymmetrical dithiopyrophosphates (RO)2P(S)SP(O)(RO)2 5 are formed in excellent yield and purity in reaction of dialkoxythioxaphosphoranesulfenyl chlorides 1 with trimethylsilylphosphites Me3SiOP(OR′)2 4. The full stereospecificity of this reaction has been demonstrated with an aid of diastereoisomeric cis- and trans-2-trimethylsilyloxy-4-methyl-1,3,2-dioxaphosphorinanes 9 which react with 1 with full retention of configuration at the phosphorus center. Preparation of diastereoisomeric cis- and trans-9 has been described and their configuration established.Keywords
This publication has 8 references indexed in Scilit:
- O,O‐Dialkyl‐thiophosphonosulfenylbromide ‐ neue Klasse reaktiver OrganophosphorverbindungenAngewandte Chemie, 1982
- Organic MonothiopyrophosphatesRussian Chemical Reviews, 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
- Axial Preference of Methylthio Substituent in Dioxaphosphorinanyl Ring SystemZeitschrift für Naturforschung B, 1975
- Stereochemistry of organophosphorus cyclic compounds—ITetrahedron, 1972
- Chemisorption of molecular hydrogen on zinc oxideJournal of the American Chemical Society, 1971
- Stereochemistry of a Michaelis–Arbusov reaction: alkylation of optically active ethyl trimethylsilyl phenylphosphonite with retention of configurationJournal of the Chemical Society D: Chemical Communications, 1971
- Conformational Dependence of P=O Stretching Vibration Frequency in Six-membered Cyclic PhosphatesBulletin of the Chemical Society of Japan, 1969