23041-33-0Relevant academic research and scientific papers
Phosphorus in organic synthesis. The tanigawa reaction revisited as a method for converting alcohols to tertiary amines
Froyen, Paul,Skramstad, Jan
, p. 6387 - 6390 (1998)
Contrary to earlier observations, N-methyl-N- phenylaminotriphenylphosphonium iodide 1 (the Murahashi reagent) does not react with alcohols and primary or secondary amines under mild conditions (80°) to give secondary or tertiary amines. However the reaction can be successfully performed at higher temperatures. A mechanistic scheme implying initial amine exchange between 1 and the added amine leading to the N,N- dimethyl analog 5 is suggested. An improved synthesis where the reactive intermediate 5 is formed in situ from triphenylphosphine, carbon tetrachloride and HNR3R4 is described.
PHOSPHORORGANISCHE VERBINDUNGEN 89 Quartaere Phosphoniumsalze mit Heteroatomen am Phosphor Herstellung, Eigenschaften und Elektroreduktive Spaltung
Horner, Leopold,Jordan, Manfred
, p. 209 - 214 (2007/10/02)
The half-potential of 35 quaternary phosphonium salts with one or more hetero-atoms attached to phosphorus are reported, and the fission products determined for the electroreduction of nine phosphonium salts.The influence of the ligands attached to phosphorus by hetero-atoms on both the half-wave potential and the course of the fission reaction is discussed.The order of precedence in the cleavage of the ligands at phosphorus is examined to determine whether a meaningful, qualitative order of stability for the corresponding ligands as free radicals can be deduced.
