The Chemistry of Organophosphorus Compounds. Volume 2. Phosphine Oxides, Sulphides, Selenides and Tellurides. Frank R. Hartley, ed., John Wiley & Sons, Chichester, 1992, xvi + 647 pp., £160.00 ISBN 0-471-93056-3

1993 ◽  
Vol 112 (4) ◽  
pp. 271-271
Author(s):  
R. A. J. Janssen
Keyword(s):  
Organophosphorus Compounds ◽  
Phosphine Oxides

Catalyst- and Solvent-Free Addition of the P–H Species to Alkenes and Alkynes: A Green Methodology for C–P Bond Formation

Synthesis ◽  
2017 ◽  
Vol 49 (21) ◽  
pp. 4783-4807 ◽  
Author(s):  
Boris Trofimov ◽  
Nina Gusarova ◽  
Nataliya Chernysheva
Keyword(s):  
Organophosphorus Compounds ◽  
Bond Formation ◽  
Solvent Free ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Secondary Phosphine Chalcogenides ◽  
Vinyl Sulfides ◽  
Radical Initiators ◽  
Phosphine Chalcogenides ◽  
Secondary Phosphines

Traditional methods for C–P bond formation via direct addition of P–H species to unsaturated compounds are usually implemented in the presence of base and metal catalysts or radical initiators in various organic solvents. During the last five years, a novel efficient and general catalyst/initiator- and solvent-free version of the hydrophosphination and hydrophosphinylation of multiple C–C bonds with H-phosphines and their chalcogenides has begun to develop and it is attracting growing attention. This approach corresponds to the recently emerged pot-, atom-, and step-economy (PASE) green paradigm. This review covers the literature on the synthesis of useful and in-demand organophosphorus compounds via catalyst- and solvent-free addition of P–H species to alkenes and alkynes.1 Introduction2 Addition of Secondary Phosphines to Alkenes3 Hydrophosphinylation of Alkenes with Secondary Phosphine Chalcogenides3.1 Oxidative Addition of Phosphine Oxides to Vinyl Sulfides3.2 Addition of Secondary Phosphine Sulfides and Phosphine Selenides to Alkenes3.3 Addition of Secondary Phosphine Sulfides and Phosphine Selenides to Divinyl Chalcogenides3.4 Hydrophosphinylation of Alkenes with Secondary Phosphine/Chalcogen Pair (Three-Component Reactions)4 Addition of Secondary Phosphines to Alkynes5 Addition of Secondary Phosphine Chalcogenides to Alkynes6 Conclusion

Organophosphorverbindungen mit tertiären Alkylsubstituenten. III*: Synthese und Reaktionen Di-1-adamantylsubstituierter Phosphorverbindungen; Kristallstruktur von Di-1-Adamantylphosphinsäurechlorid / Organophosphorus Compounds with Tertiary Alkyl Substituents. Ill: Synthesis and Reactions of Di-1-adam antyl-Substituted Phosphorus Compounds; Crystal Structure of Di-1-adam antylphosphinic Chloride

1994 ◽  
Vol 49 (6) ◽  
pp. 801-811 ◽  
Author(s):  
Jens R. Goerlich ◽  
Axel Fischer ◽  
Peter G. Jones ◽  
Reinhard Schmutzler
Keyword(s):  
Organophosphorus Compounds ◽  
Phosphorus Compounds ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
X Ray ◽  
Dry Air ◽  
Nmr Data ◽  
Standard Procedures ◽  
Hydrolysis Of ◽  
Tertiary Alkyl

The reaction of adamantane with PCl3/A1Cl3, followed by hydrolysis, gave (1-Ad)2P(:O)Cl 1, which was converted to (1-Ad)2P(:O)F 2 and (1-Ad)2P(:S)Cl 3 by standard procedures. The structure of 1 was confirmed by a single crystal X-ray structure determination; despite the bulky substituents the P-C bond lengths are normal (184.0(3), 185.0(3) pm). Whereas chlorine-fluorine exchange in 3 with AsF3 furnished (1-Ad)2P(:S)F 4, desulfuration of 3 with Ph3P to give (1-Ad)2PCl 5 failed. The secondary phosphine oxides R 1R2P(:O)H (R1, R2 = 1-Ad: 6; R1 = 1-Ad, R2 = tBu: 7; R1, R2 = tBu: 8) were synthesized by reaction of 1, 1-AdP(:O)Cl2 and tBuP(:0)Cl2 with tBuLi. 6 and 8 reacted readily with chloral to give the adducts R2P(:O)CH(OH)CCl3 (R = 1-Ad: 9; R = tBu: 10). Silylation of 6 with Me2NSiMe3 in the presence of dry air led to (1-Ad)2P(:O)OSiMe3 11, which was hydrolyzed to give (1-Ad)2P(:O)OH 12. (1-Ad)2POSiMe3 13 was obtained by the reaction of 6 with n-BuLi, followed by Me3SiCl. No reaction took place upon heating 6 with Mo(CO)6. (1-Ad)2PCl 5 was synthesized in low yield by the reaction of 6 with PCl3. The action of tetrachloro-obenzoquinone (TOB) upon 6 furnished (1-Ad)2P(:O)(o-OH)C6Cl4 15, whereas the tbutyl analogue of 15, 16, was synthesized by hydrolysis of the TOB-adduct of di-tbutylfluorophosphine. Analogous 1-adamantyl- and tbutyl-phosphorus compounds are compared with regard to their 31P NMR data

Organophosphorus compounds. XVI. 2-(N-Dialkylamino)alkyldiphenylphosphines, phosphine oxides and sulphides as analogues of methadone

1974 ◽  
Vol 27 (11) ◽  
pp. 2365 ◽  
Author(s):  
DJ Collins ◽  
S Mollard ◽  
N Rose ◽  
JM Swan
Keyword(s):  
Analgesic Activity ◽  
Secondary Amine ◽  
Organophosphorus Compounds ◽  
Phosphine Oxides ◽  
Reaction Conditions ◽  
Diphenylvinylphosphine Oxide

A series of 2-(N-dialkylamino)ethyldiphenylphosphine oxides and sulphides was prepared by the addition of a secondary amine to diphenylvinylphosphine oxide, or the phosphine sulphide, respectively. Similarly, a series of 2-(N-dialkylamino)propyldiphenylphosphine oxides was prepared from diphenylprop-1-enylphosphine oxide, or from diphenylprop-2-enylphosphine oxide which isomerized under the reaction conditions. Reduction of the 2-(N-dialkylamino)propyldiphenylphosphine oxides with trichlorosilane, and oxidation of the phosphines with sulphur, afforded the corresponding phosphine sulphides. ��� None of the compounds showed significant analgesic activity.

SPECTROSCOPIC STUDIES OF ORGANOPHOSPHORUS COMPOUNDS: PART I. THE CONSTITUTION OF ALKYLPHOSPHINE – CARBON DISULFIDE ADDUCTS

1965 ◽  
Vol 43 (3) ◽  
pp. 608-613 ◽  
Author(s):  
M. Arshad A. Beg ◽  
M. S. Siddiqui
Keyword(s):  
Carbon Disulfide ◽  
Infrared Spectra ◽  
Organophosphorus Compounds ◽  
Spectroscopic Studies ◽  
Phosphorus Compound ◽  
Acceptor Molecule ◽  
Phosphine Oxides

The constitution of the alkylphosphine – carbon disulfide adducts has been investigated by the study of their infrared spectra. Certain definite features of the spectra of the adducts are the shift of the P—C asymmetric vibrations to higher frequencies and the large shifts in the fundamentals of the acceptor molecule. These features are attributed to the formation of a quadruply connected phosphorus compound. From a comparison of the spectra of the carbon disulfide adducts with those of the corresponding phosphonium compounds, phosphine oxides and phosphines, evidence is provided for the structure of these compounds which has been suggested to be of the phosphonium type.

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