27286-15-3Relevant academic research and scientific papers
Synthesis of phosphiranes
Kolodyazhnaya,Kolodyazhnyi
, p. 436 - 440 (2015/04/14)
Phosphiranes, three-membered phosphorus-containing heterocycles, have been prepared via reaction of tertiary phosphines dilithium derivatives with carbon tetrachloride. The elaborated method can be applied for preparation of some phosphiranes which are not easily accessible.
Synthesis of Anti-Cis-Phosphiranes
Kolodiazhna, Olga O.,Kolodiazhnyi, Oleg I.
, p. 1192 - 1200 (2015/08/04)
A method for the preparation of three-membered phosphoric heterocycles-phosphi-ranes by reaction of dilithium derivatives of tertiary phosphines with tetrachloromethane is described. The reaction is stereoselective and leads to the formation of anti-cis(meso)-2,3-diphenylphosphiranes. Phosphiranes were isolated as individual compounds and their structure was confirmed by 1H, 13C, and 31P NMR spectra, and mass spectra. The present method is simple and can be successfully used for the preparation of some types of phosphiranes that are inaccessible by other methods.
Three-membered Ring Heterocycles, 14. α-Halogenation of Tertiary Phosphane Oxides
Heuschmann, Manfred,Quast, Helmut
, p. 3384 - 3401 (2007/10/02)
The symmetrically substituted tertiary phosphane oxides 5 were obtained from phosphorus halides 4 and 6 using organometallic reagents.Dibenzylphenylphosphane oxide (5c) reacted with bromine at 150 deg C to give all three possible diastereomeric α,α'-dibromophosphane oxides. e.g. (R,R/S,S)-2c, (r)-2c, and (s)-2c, and one α-bromophosphane oxide 8.The phosphane oxides 5a, b, d were lithiated once or twice in the α-positions by means of butyllithium.The α,α'-dilithiophoasphane oxides -5 reacted with tetrachloromethane below -80 deg C to yield the α-chlorophosphane oxides 1c - e whose diastereomeric ratios were controlled kinetically.The thermodynamically controlled ratios were adjusted with bases.While the α-lithiated dineopentyl phosphane oxides -5a and -5d also afforded the α-chlorophosphane oxides 1c and 1d, respectively, with an excess of tetrachloromethane, the α,α-dichlorophosphane oxide 9 was formed from the α-lithiobenzylphosphane oxide 5b.This difference is attributed to the acidity of the α-protons and steric factors.The configurations and preferred conformations of the α,α'-dibromophosphane oxides 2c and the α-chlorophosphane oxides 1c - e were determined on the basis of the 1H-31P coupling of the methine protons.
