87763-18-6Relevant academic research and scientific papers
Hydrophosphonylation of Alkynes with Trialkyl Phosphites Catalyzed by Nickel
Islas, Rosa E.,García, Juventino J.
, p. 4125 - 4131 (2017/10/09)
The use of simple and inexpensive NiCl2?6 H2O as a catalyst precursor for C?P bond formation in the presence of commercially available trialkyl phosphites (P(OR)3, R=Et, iPr, Bu, SiMe3) along with several alkynes is presented. Control experiments showed the in situ formation of (RO)2P(O)H as the species that undergo the addition into the C≡C bond at the alkynes to yield the product of P?H addition. The hydrophosphonylation of diphenylacetylene with P(OEt)3, P(OiPr)3, and P(OSiMe3)3 proceeds in high yields (>92 %) without the need of a specific solvent or ligand. This method is useful for the preparation of organophosphonates for both phenylacetylene as a terminal alkyne model and internal alkynes in yields that range from good to modest.
Reactions of Ethyl phosphites with β-Nitrostyrenes. The Role of Nitrosoalkenes as Intermediates
Russell, Glen A.,Yao, Ching-Fa
, p. 6508 - 6513 (2007/10/02)
3-Phenyl-2-substituted-indoles are formed in high yields in the reaction of Ph2C=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150 deg C while reaction with (EtO)2PO(1-)/(Et2O)P(O)H at room temperature forms the aziridines 1 with R = H, Me, Ph. 2,2-Diphenyl-3-substituted-2H-azirines formed by deoxygenation of the Michael-type aducts are postulated as intermediates.Reactions of PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150 deg C or (EtO)2PO(1-)/(EtO)2P(O)H at room temperature give products resulting from the addition of the phosphorus nucleophile at the benzylidene carbonatom.Evidence for the formation of cyclic structures with pentacoordinated phosphorus atoms is presented for the reaction of Ph2C=C(Me)NO2 with (EtO)2PO(1-)/(EtO)2P(O)H and for PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P.The Michael-type adducts PhCHCH(R)NO2 (R = Me, Ph) undergo reaction upon treatment with aqueous base at 80-100 deg C followed by acidification to yield the 3-(diethoxyphosphinyl)-2-R-N-hydroxyindoles. 4-(Diethoxyphosphinyl)-3-R-4H-1,2-benzoxazines (13, R = Me, Ph) are formed by reaction with 85percent H2SO4 of the adducts of PhCH=C(R)NO2 with (EtO)2PO(1-) (R = Me) or (EtO)3P (R = Ph).
Synthesis and Reactions of Phosphoryl-Substituted Sulfines
Porskamp, Pascal A. T. W.,Lammerink, Ben H. M.,Zwanenburg, Binne
, p. 263 - 268 (2007/10/02)
The synthesis of a variety of phosphoryl-substituted sulfines 5 by the reaction of α-silyl carbanions with sulfur dioxide is described.For characterization purposes the prepared sulfines were converted into their cycloadducts 6 with 2,3-dimethyl-1,3-butad
