Synthesis of New Phosphonate Derivatives of Naphtho[2,1-b[Pyran]3,2-e][1,2,4]Triazolo [1,5-c]Pyrimidines

Abstract

The synthesis of new naphthopyranotriazolopyrimidines phosphonates 4a–i in good yields (74%–93%) has been accomplished via Michaelis–Arbusov rearrangement by the reaction of trialkyl phosphite with naphthopyranotriazolopyrimidines chloride 3a–e, which were obtained from α-functionalized iminoethers 1 in two steps. The synthesized compounds 4a–i were completely characterized by IR, ¹H, ¹³C, and ³¹P NMR and HRMS.

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ETUDE DE QUELQUES REACTIONS DE LA TRIS(TERT-BUTYL)PHENYLPHOSPHINE

Abstract

The reaction of tris(tert-butyl)phenylphosphine with some hydrogen acceptors has been investigated. Triphenylcarbenium hexafluorophosphate allows to obtain a phosphonium salt: the possibility of preliminary formation of phosphenium with a P[sbnd]H bond during this reaction is discussed. With methyltrifluoromethanesulfonate, two pentacoordinated phosphorus compounds are isolated. Diethylazodicarboxylate gives rise to a σ³, λ⁵-phosphorane. The transient formation of phosphinidene and of 1,2-bis(ethylcarboxylate) 3-tris(tert-butyl)phenyldiazaphosphirine is discussed.     

A Novel and Efficient Synthesis of α-Aminophosphonates by Use of Triphenyl Phosphite in Acetic Acid Media

Abstract

For the first time, α-aminophosphonates were obtained by a simple and efficient one-pot method from the reaction between aldehyde, aniline, and triphenyl phosphite in the presence of acetic acid as a catalyst and solvent at room temperature.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

GRAPHICAL ABSTRACT     

Trimethyl borate-induced one-pot homologation reactions of isoquinoline with di-tert-butyl-TMP zincate

Novel one-pot homologation reactions of isoquinoline and quinoline with di-tert-butyl-TMP zincate/trimethyl borate are described. 1-tert-Butyl-3,4-dihydroisoquinoline 1 and 1-tert-butylisoquinoline 2 are formed unexpectedly under the presented reaction conditions with relative ease. A reaction mechanism, including 1,2-migration of the tert-butyl group from 1-isoquinolylzincate, is proposed in detail. Migratory aptitudes of other ligands of isoquinolyl zincates are also discussed.     

含金刚烷基团的新型手性单齿亚磷酸酯配体的合成及其在不对称1,4-共轭加成反应中的应用

以轴手性的BINOL/H8-BINOL(BINOL为联苯酚)和大位阻的金刚烷酰氯为原料,合成了系列新型手性单齿亚磷酸酯配体,并应用于Cu催化的二乙基锌对环烯酮的不对称1,4.共轭加成反应中.结果表明,配体结构中部分氢化的2,2'-(1,1'-联萘基)亚磷酸酯单元和金刚烷基团,有助于改善反应的对映选择性,对映选择性最高可...     

NMR relaxation study of disorder in the mixed system BP x GPI(1–x) and the low temperature transition from classical to quantum rotation

¹H NMR spin-lattice relaxation time (T ₁) studies have been carried out in the temperature range 100 K to 4 K, at two Larmor frequencies 11.4 and 23.3 MHz, in the mixed system of betaine phosphate and glycine phosphite (BP_xGPI_(1–x)), to study the effects of disorder on the proton group dynamics. Analysis of T ₁ data indicates the presence of a number of inequivalent methyl groups and a gradual transition from classical reorientations to quantum tunneling rotations. At lower temperatures, microstructural disorder in the local environments of the methyl groups, result in a distribution in the activation energy (E_a ) and the torsional energy gap (E ₀₁). For certain values of x, the magnetisation recovery shows biexponential behaviour at lower temperatures.     

Formal Aniline Synthesis from Phenols through Deoxygenative N-Centered Radical Substitution

Phenolic, lignin-derived substrates have emerged as desirable biorenewable chemical feedstocks for coupling reactions. A radical-mediated conversion of phenol derivatives to anilines is reported, using unfunctionalized hydroxamic acids as the N-centered radical source. The applicability of this triethyl phosphite mediated O-atom transfer approach, which tolerates a range of steric and electronic demands to naturally occurring phenols and lignin models, has been demonstrated in this work to access the corresponding aniline derivatives.     

Nanoribbon‐Structured Organo Zinc Phosphite Polymorphs with White‐Light Photoluminescence

The first neutral organo zinc phosphites composed of 2.8 nm‐wide ribbons were obtained in pure phases and exhibit near‐white‐light photoluminescence (PL). By using the “mesitylene strategy”, interesting polymorphism in the system of NTHU‐14 was discovered. The S‐shaped ribbons are arranged into R and L arrays, resulting in RLR and RRR stacking for two polymorphs. π–π interactions exist within each array and hydrogen bonding between adjacent arrays. Besides a common ligand‐based emission band at 410 nm, the PL curves of polymorphs 14‐α and 14‐β are distinctly different: 14‐α gave a defect‐based emission at 565 nm, whereas 14‐β primarily shows a π‐excimer‐based emission at 535 nm. Electron paramagnetic resonance (EPR) data disclosed that radical species exist in the reaction and that the two phases were growing from different environments. Based on these results, the origin of the 565 nm band can be ascribed to lattice defects, and one possible cause of 14‐β not showing noticeable yellow emission is identified.     

Synthesis and properties of poly(amide-imide)s derived from trimellitic anhydride, ω-amino acids,and aromatic diamines

Seven imidodicarboxylic acids II -1 to 5, II -10, and II -11 were prepared from trimellitic anhydride and ω-amino acids, such as glycine, β-alanine, 4-aminobutyric acid, 5-aminopentanoic acid, 6-aminohexanoic acid, 11-aminoundecanoic acid, and 12-aminododecanoic acid. Several aliphatic-aromatic poly(amide-imide)s were prepared by triphenyl phosphite promoted polycondensation reaction from the combination of 3-(4-carboxyphthalimido)propionic acid ( II -2) or 6-(4-carboxyphtalimido)hexanoic acid ( II -5) with various aromatic diamines and of all the imidodiacids with p-phenylenediamine or 4,4′-oxydianiline. All poly(amide-imide)s were characterized by inherent viscosity, gel permeation chromatography (GPC) measurements, solubility, tensile test, wide-angle X-ray scatting patterns, differential scanning calorimetry (DSC) measurements, and thermogravimetric (TGA) analyses. Effects of structural changes such as polymethylene length and diamine moieties on the properties of poly(amide-imide)s were studied. © 1994 John Wiley & Sons, Inc.     

一锅反应合成1-羟基-3-苯基烯丙基膦(次膦)酸酯

1-羟基膦酸酯类化合物具有显著的生物活性和潜在的医学用途,从五十年代起,不断有新的或改良的合成方法出现。但这些方法并不理想,常伴有副反应等。近年来发展了用