ChemInform Abstract: STEREOCHEMISTRY OF ORGANOPHOSPHORUS COMPOUNDS. XII. NEW DIAZOALKANES WITH A CHIRAL PHOSPHORUS ATOM

1977 ◽  
Vol 8 (1) ◽  
pp. no-no
Author(s):  
R. D. GAREEV ◽  
YU. YU. SAMITOV ◽  
A. N. PUDOVIK
Keyword(s):  
Phosphorus Atom ◽  
Organophosphorus Compounds

Asymmetric Synthesis of Organophosphorus Compounds using H-P reagents derived from Chiral Alcohols

2021 ◽  
Author(s):  
Tomasz K. Olszewski ◽  
Joseph Gbubele
Keyword(s):  
Asymmetric Synthesis ◽  
Phosphorus Atom ◽  
Organophosphorus Compounds ◽  
Chiral Alcohols

Chiral organophosphorus compounds, especially those containing C-stereogenic carbons in the proximity of the phosphorus atom, are known for their unique properties and have found wide applications that span from medicinal...

scholarly journals Organophosphorverbindungen mit tertiären Alkylsubstituenten, II*: Synthese und Charakterisierung triphenylmethylsubstituierter λ4P(V)-Verbindungen; Kristallstruktur von Triphenylmethyl-Phosphonsäuredifluorid / Organophosphorus Compounds with Tertiary Alkyl Substituents, II*:Synthesis and Characterization of Triphenylmethyl-Substituted λ4P(V) Compounds;Crystal Structure of Triphenylmethylphosphonic Difluoride

1993 ◽  
Vol 48 (3) ◽  
pp. 341-347 ◽  
Author(s):  
Jens R. Goerlich ◽  
Axel Fischer ◽  
Peter G. Jones ◽  
Volker Plack ◽  
Reinhard Schmutzler
Keyword(s):  
Crystal Structure ◽  
Single Crystal ◽  
Phosphorus Atom ◽  
Organophosphorus Compounds ◽  
Synthesis And Characterization ◽  
X Ray ◽  
Nmr Parameters ◽  
Microwave Spectra ◽  
Tertiary Alkyl

The synthesis of the triphenylmethyl-phosphonic and -phosphonothioic dihalides Ph3CP(:X)Y2 (X = O, S; Y = F, Cl) is described. The NMR parameters of these compounds are discussed and compared to these of other phosphonic and thiophosphonic dihalides. Single crystal X-ray analysis was used to confirm the structure of Ph3CP(:O)F2 2 [C2/c, a = 1599.6(4), b = 1096.3(3), c = 1863.1(7) pm, ß = 109.11(2)°, T = 178 K, R = 0.034]. The geometry at the phosphorus atom is approximately tetrahedral. The bonds between phosphorus and fluorine are extremely short [P— F 153.1(1) and 153.3(1) pm]. Bond distances and angles for this compound are compared to those of methylphosphonic difluoride which were obtained from microwave spectra.

scholarly journals Synthesis of diphenylphosphinic acid esters

2017 ◽  
Vol 72 (1) ◽  
pp. 23
Author(s):  
Ewelina Korzeniowska
Keyword(s):  
Organic Chemistry ◽  
Asymmetric Catalysis ◽  
Organic Synthesis ◽  
Phosphorus Atom ◽  
Organophosphorus Compounds ◽  
High Demand ◽  
New Methods ◽  
Acid Esters

<p>The development of new methods for the synthesis of organophosphorus compounds is still an important part of organic chemistry due to the high demand for these compounds in organic synthesis as well as in asymmetric catalysis. Most of the methods for the synthesis of these compounds include the reactivity of the phosphorus atom, which depending on the structure might exhibit both electrophilic and nucleophilic properties. Herein, I will present the results concerning synthesis of diphenylphosphinic acid esters.</p>

Organophosphorus compounds. VII. Electron-impact fragmentations of esters of phosphonic acids

1966 ◽  
Vol 19 (7) ◽  
pp. 1187 ◽  
Author(s):  
JL Occolowitz ◽  
JM Swan
Keyword(s):  
Electron Impact ◽  
Phosphorus Atom ◽  
Mass Spectra ◽  
Organophosphorus Compounds ◽  
Ester Group ◽  
Base Peak ◽  
Phosphonic Acids ◽  
Hydrocarbon Group ◽  
Carbon Fragment ◽  
Hydro Carbon

The mass spectra of some dialkyl and diaryl esters of a variety of alkyl-, alkenyl-, alkynyl-, and aryl-phosphonic acids are discussed. The spectra are in many cases similar to those observed for simple dialkyl alkylphosphonates, but with some important differences depending on the nature of the hydrocarbon group attached directly to the phosphorus atom. Some unusual rearrangements are observed, involving migration of a hydro-carbon fragment from the ester group to the hydrocarbon moiety attached to phosphorus, with simultaneous expulsion of a phosphinyl radical. Thus diethyl vinylphosphonate gives an ion [C4H7]+; diethyl 2-phenylvinylphosphonate gives a base peak at m/e 131 due to PhCH=CHCHCH3; diphenyl 2-phenylvinylphosphonate gives an ion [C14H12O]+', and from this, an ion [C14H10]+ which can be formulated as the molecular ion of phenanthrene.

scholarly journals Primary Phosphines and Phosphine Oxides with a Stereogenic Carbon Center Adjacent to the Phosphorus Atom: Synthesis and Anti-Markovnikov Radical Addition to Alkenes

Organics ◽  
2021 ◽  
Vol 2 (4) ◽  
pp. 395-403
Author(s):  
Toshiaki Murai ◽  
Ryota Wada ◽  
Kouji Iwata ◽  
Yuuki Maekawa ◽  
Kazuma Kuwabara ◽  
...  
Keyword(s):  
Carbon Atom ◽  
Phosphorus Atom ◽  
Organophosphorus Compounds ◽  
Radical Addition ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Reaction Conditions ◽  
High Yields ◽  
Oxidized Products

Organophosphorus compounds with stereogenic phosphorus and carbon atoms have received increasing attention. In this regards, primary phosphines with a stereogenic carbon atom adjacent to the phosphorus atom were synthesized by the reduction in phosphonates and phosphonoselenoates with a binaphthyl group. Their oxidized products, i.e., phosphine oxides with a stereogenic tetrasubstituted carbon atom, were found to undergo BEt3-mediated radical addition to cyclohexene to give P-stereogenic secondary phosphine oxides with a diastereoselectivity of 91:9. The products were characterized by ordinary analytical methods, such as Fourier transform infrared spectroscopy; 1H, 13C, and 31P NMR spectroscopies; and mass spectroscopy. Computational studies on the phosphorus-centered radical species and the obtained product implied that the thermodynamically stable radical and the adduct may be formed as a major diastereomer. The radical addition to a range of alkenes took place in an anti-Markovnikov fashion to give P-stereogenic secondary phosphine oxides. A variety of functional groups in the alkenes were tolerated under the reaction conditions to afford secondary phosphine oxides in moderate yields. Primary phosphines with an alkenyl group, which were generated in situ, underwent intramolecular cyclization to give five- and six-membered cyclic phosphines in high yields after protection by BH3.

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