scholarly journals Cleavage of the carbon–phosphorus bond in chloromethyl–phosphorus compounds by phosphorus pentachloride

1968 ◽  
Vol 46 (22) ◽  
pp. 3573-3577 ◽  
Author(s):  
Arlen W. Frank
Keyword(s):  
Carbon Tetrachloride ◽  
Phosphine Oxide ◽  
Bond Cleavage ◽  
Phosphorus Pentachloride ◽  
Phosphorus Trichloride ◽  
Phosphorus Compounds ◽  
Concerted Mechanism ◽  
Phosphonium Chloride

A novel carbon–phosphorus bond cleavage is described. Chloromethylphosphonic dichloride (2) and bis(chloromethyl)phosphinic chloride (1) both react smoothly and quantitatively with phosphorus pentachloride at 95–100°, giving carbon tetrachloride and a P(III) fragment containing one less carbon–phosphorus bond: phosphorus trichloride from 2 and trichloromethylphosphonous dichloride from 1. Under the same conditions, tris(chloromethyl)phosphine oxide (3) forms a complex (4) which subsequently breaks down to trichlorobis(trichloromethyl)phosphorane (5), diphenyl chloromethylphosphonate (7) suffers chlorination without cleavage, and tetrakis(chloromethyl)phosphonium chloride (6) is neither chlorinated nor cleaved. A concerted mechanism is proposed which accounts for ail of these results.

ORGANIC PHOSPHORUS COMPOUNDS: II: PREPARATION OF CHLOROMETHANEPHOSPHONYL DICHLORIDE

1953 ◽  
Vol 31 (10) ◽  
pp. 976-983 ◽  
Author(s):  
R. A. B. Bannard ◽  
J. R. Gilpin ◽  
G. R. Vavasour ◽  
A. F. McKay
Keyword(s):  
Atmospheric Pressure ◽  
Phosphorus Oxychloride ◽  
Organic Phosphorus ◽  
Phosphorus Pentachloride ◽  
Heating Time ◽  
Phosphorus Trichloride ◽  
The Other ◽  
Phosphorus Compounds ◽  
Subsequent Hydrolysis ◽  
Hydrolysis Of

Hydroxymethanephosphonic acid was prepared by treating paraformaldehyde with phosphorus trichloride at atmospheric pressure and subsequent hydrolysis of the resultant complex. Chloromethanephosphonyl dichloride was obtained by chlorination of hydroxymethanephosphonic acid with thionyl.chloride in the presence of pyridine. On the other hand hydroxymethanephosphonic acid combined slowly with phosphorus pentachloride to give the hitherto unknown dichlorophosphorylmethanephosphonyl dichloride, Cl2P(O)OCH2P(O)Cl2, together with chloromethanephosphonyl dichloride. The structure of dichlorophosphorylmethanephosphonyl dichloride was confirmed by its conversion with phosphorus pentachloride at 78 °C into chloromethanephosphonyl dichloride and phosphorus oxychloride. The preparation of chloromethanephosphonyl dichloride by interaction of paraformaldehyde and phosphorus trichloride in an autoclave at 250 °C was studied in reference to the influence of heating time on the yield.

Ab Initio Study of Carbon−Chlorine Bond Cleavage in Carbon Tetrachloride

2005 ◽  
Vol 39 (2) ◽  
pp. 612-617 ◽  
Author(s):  
Nianliu Zhang ◽  
Paul Blowers ◽  
James Farrell
Keyword(s):  
Carbon Tetrachloride ◽  
Ab Initio ◽  
Bond Cleavage ◽  
Ab Initio Study ◽  
Chlorine Bond

Effect of pH on the Phosphorous Components in Tetra-Hydroxymethyl Phosphonium Chloride Solution

2012 ◽  
Vol 560-561 ◽  
pp. 237-241 ◽  
Author(s):  
Shuang Xi Shao ◽  
Lan Jiang ◽  
Ya Li ◽  
Kai Qi Shi
Keyword(s):  
Water Treatment ◽  
Flame Retardant ◽  
Chloride Solution ◽  
31P Nmr ◽  
Phosphorus Compounds ◽  
Industrial Water ◽  
Nuclear Magnetism ◽  
Phosphonium Chloride ◽  
Actual Application ◽  
Manufacture Industry

At present, tetra-hydroxymethyl phosphonium chloride (THPC) is widely used in flame retardant finishing, industrial water treatment and leather manufacture industry etc., and its decomposition which was caused by pH changing will influence on the actual application. So acid-alkali decomposition of THPC was studied by 31P Nuclear Magnetism Resomance (31P NMR), spectrophotometry and titration respectively. The results show that THPC solution is stable when pH9.0, all of the phosphorus compounds converts to TrHPO. Consequently, THPC content decreases when pH of the THPC solution rising, which could give a favorable guide in THPC application.

Chemoselectivity for B–O and B–H Bond Cleavage by Pincer-Type Phosphorus Compounds: Theoretical and Experimental Studies

2020 ◽  
Vol 59 (21) ◽  
pp. 15636-15645 ◽  
Author(s):  
Qin Zhu ◽  
Penglong Wang ◽  
Jun Zhu ◽  
Congqing Zhu ◽  
Guixiang Zeng
Keyword(s):  
Bond Cleavage ◽  
Experimental Studies ◽  
Phosphorus Compounds

Synthesis of a Flame Retardant Containing Nitrogen-Phosphor and its Application on Silk Fabric

2012 ◽  
Vol 441 ◽  
pp. 447-451 ◽  
Author(s):  
Yu Mei Yang ◽  
Jin Ping Guan ◽  
Guo Qiang Chen
Keyword(s):  
Carbon Tetrachloride ◽  
Flame Retardant ◽  
Phosphorus Trichloride ◽  
Silk Fabric ◽  
Technological Parameters ◽  
Methacryloyl Chloride ◽  
Water Emulsion ◽  
Oil In Water ◽  
Char Length ◽  
Oil In Water Emulsion

In this paper, a flame retardant methacryloyl ethyl diethyl phosphoric amide (PN) containing nitrogen-phosphor for textiles was synthesized from phosphorus trichloride, absolute ethylalcohol, carbon tetrachloride, monoethanol amine, methacryloyl chloride. PN oil-in-water emulsion was grafted onto silk fabric by Atom Transfer Radical Polymerization (ATRP) method. The grafting technological parameters were investigated. The flame retardancy property of the treated silk fabric was indicated by LOI value, char length, after flame and after glow time.

Unprecedented Reactivity of Iridium(I) Secondary Phosphine Oxide Complexes: Formation of P-Coordinated Phosphinate Complexes by P−Aryl Bond Cleavage

2010 ◽  
Vol 29 (22) ◽  
pp. 5953-5958 ◽  
Author(s):  
Marc Liniger ◽  
Björn Gschwend ◽  
Markus Neuburger ◽  
Silvia Schaffner ◽  
Andreas Pfaltz
Keyword(s):  
Phosphine Oxide ◽  
Bond Cleavage ◽  
Secondary Phosphine

THE EASY P—C-BOND CLEAVAGE OF FLUORINATED PHOSPHINE OXIDE

1993 ◽  
Vol 84 (1-4) ◽  
pp. 249-251 ◽  
Author(s):  
A. Yu. Aksinenko ◽  
A. N. Pushin ◽  
V. B. Sokolov
Keyword(s):  
Phosphine Oxide ◽  
Bond Cleavage
Sign in / Sign up

Export Citation Format

Share Document