193554-97-1Relevant academic research and scientific papers
Synthesis of racemic P-chiral phosphine oxides and phosphonium salts by stepwise reaction of phosphacoumarins with organomagnesium compounds
Fayzullin, Robert R.,Kuznetsov, Denis M.,Mironov, Vladimir F.,Tatarinov, Dmitry A.
, (2020)
A new effective synthetic route to the racemic phosphine oxides and phosphonium salts with a P-asymmetric center was developed based on the stepwise reaction of phosphacoumarins with organomagnesium compounds. A selective P–C bond formation was achieved on each step owing to the differences in reactivity of the exocyclic P–Cl or P–O bonds and endocyclic P–O bond of phosphacoumarins. It was found that the P(O)OMgX fragment of the phosphocoumarin salt does not hinder in the substitution reaction at the phosphorus atom accompanied by ring-opening and P–C bond formation.
Reactions of phenylenedioxytrihalophosphoranes with arylacetylenes: XIII. Reaction of 5-tert-butyl-2,2,2-trihalo-1,3,2λ5- benzodioxaphospholes with acetylenes
Mironov,Nemtarev,Varaksina,Shtyrlina,Gubaidullin,Litvinov,Dobrynin
, p. 864 - 887 (2014/08/18)
Reactions of 5-tert-butyl-2,2,2-trichloro-, 2,2,2-tribromo-5-tert-butyl-, and 2,2-dibromo-5-tert-butyl-2-fluoro-1,3,2λ5- benzodioxaphospholes with aryl- and alkylacetylenes lead to quantitative formation of 2-halo-1,2λ5-benzoxaphosph
Synthesis and chemical properties of benzo[e]-1,2-oxaphosphorinine derivatives - Analogues of coumarins
Varaksina,Tatarinov,Cherkin,Nemtarev,Mironov,Konovalov
body text, p. 566 - 570 (2009/04/06)
The 4-aryl(alkyl)benzo[e]-1,2-oxaphosphorine derivatives (phosphacoumarins) were obtained by the reaction of 2,2,2-trihalogenobenzo[d]-1,3,2- dioxaphospholes with terminal acetylenes. The reactions of phosphacoumarins with halogens and Grignard reagents w
Reactions of trihalo(phenylenedioxy)phosphoranes with arylacetylenes: IX.* reaction of 2,2,2-trichloro-1,3,2λ5- benzodioxaphosphole with 1-iodo-2-phenylethyne
Mironov,Varaksina,Shtyrlina,Musin,Konovalov
, p. 118 - 123 (2007/10/03)
According to NMR data, the reaction of 2,2,2-trichloro-1,3, 2λ5-benzodioxaphosphole with 1-iodo-2-phenylethyne leads to formation of 2,6- and 2,8-dichloro-3-iodo-4-phenyl-1,2λ5- benzoxaphosphinine 2-oxides which undergo partial hydro
Reaction of trihalo(phenylenedioxy)phosphoranes with arylacetylenes: VII. Regiochemistry of reaction 2,2,2-tribromo-5-halobenzo[d]-[1,3, 2λ5]dioxaphospholes with arylacetylenes
Mironov,Azancheev,Musin,Konovalov
, p. 541 - 548 (2007/10/03)
It was for the first time shown that 2,2,2-tribromo- and 2,2-dibromo-2-fluoro-5-halobenzo[d]-[1,3,2λ5]dioxaphospholes react with arylacetylenes with preferential formation of heterocycles monohalogenated in the benzo fragment, viz. 4-aryl-2-bromo(fluoro)-7- halobenzo[e][1,2]oxaphosphinines. Their structure was established by NMR spectroscopy. By varying in such a way the nature of the halogen at the phosphorus atom one can obtain 6- or 7-halo-substituted regioisomers of benzo[e][1,2]oxaphosphinines. 2005 Pleiades Publishing, Inc.
Regiochemistry of the reactions of phenylenedioxytrichlorophosphorane with phenylacetylene and propargyl chloride in the presence of benzyltrimethylammonium chloride
Mironov,Shtyrlina,Konovalov,Varaksina,Azancheev
, p. 745 - 747 (2007/10/03)
NMR studies revealed that the reactions of phenylenedioxytrichlorophosphorane with phenylacetylene and propargyl chloride in the presence of benzyltrimethylammonium chloride predominantly yield derivatives of 2,7-dichloro-2-oxobenzo[e]-1,2-oxaphosphorinin
Reaction of phenylenedioxytrihalophosphoranes with arylacetylenes: II.1 Synthesis and steric structure of 6,7-dihalo-2-hydroxy-2-oxo-4-phenylbenzo[e]-1,2λ5-oxaphosphori n-3-enes
Mironov,Litvinov,Shtyrlina,Gubaidullin,Petrov,Konovalov,Azancheev,Musin
, p. 1046 - 1061 (2007/10/03)
High-resolution mass spectrometry and NMR and IR spectroscopy were used to show that the products of reaction of 2,2,2,5-tetrachlorobenzo[d]-1,3,2λ5-dioxaphosphole and 5-bromo-2,2,2-trichlorobenzo-[d]-1,3,2λ5-dioxaphosphole with phenyl- and para-bromophenylacetylenes are trihalogenated six-membered heterocycles, 2,6,7-trichloro-2-oxo-4-phenylbenzo[e]- and 4-aryl-7-bromo-2,6-dichloro-2-oxobenzo[e]-1,2λ5-oxaphosphorin- 3-enes. The steric structure of the 2-hydroxy derivatives formed by hydrolysis of the latter was studied by X-ray diffraction.
Reaction of phenylenedioxytrihalogenophosphoranes with arylacetylenes. Synthesis and spatial structure of the derivatives of 2-oxo-4-aryl-5,6-benzo-1,2-oxaphosphorin-2-enes
Mironov, Vladimir F.,Gubaidullin, Aidar T.,Petrov, Ravil R.,Litvinov, Igor A.,Shtyrlina, Alfiya A.,Zyablikova, Tatyana A.,Azancheev, Nail M.,Konovalov, Alexander I.,Musin, Rashid Z.
, p. 377 - 380 (2007/10/03)
New method of synthesis of six-membered heterocycles - 2-R-2-oxo-4-aryl-2H-benzo[e][1,2]-oxaphosphorin-3-enes has been developed. It includes the interaction of arylenedioxy trihalogenophosphoranes with arylacetylenes. The formation of phosphoryl group and P-C bond, ipso-substitution of the aromatic oxygen and halogenation of the benzene ring take place in this unusual reaction. The influence of the phosphorane structure on synthetic result is discussed. If both para positions at benzene ring of the phosphorane are occupated by halogens, the evolving of halogen molecule occurs. The structures of 2-R-2-oxo-4-aryl-2H-benzo[e][1,2]-oxaphosphorin-3-enes are determined by X-ray analysis.
