Two Methods for the Synthesis of (2-Mercaptophenyl)phosphonic Acid

Masson, Serge; Saint‐Clair, Jean‐Francois; Saquet, Monique

doi:10.1055/s-1993-25889

Cited by 44 publications

(15 citation statements)

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“…This surprising result together with the lack of reactivity in other solvents suggests that DMSO might act not only as the solvent but also as an oxidant in the reaction. [24,25] Also, we investigated the loading of catalyst and found that the optimal dosage of cesium hydroxide was 20 mol% (Table 1, entries [12][13][14].…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8][9][10] General methods for the preparation of phosphorochalcogenoates esters bearing thio and=or seleno substituents have been well documented. [11][12][13][14][15] However, as congener element, there are a few reports for the preparation of Te-aryl phosphorotelluroates; therefore only little was known about their reactivities, although the phosphorotellurate esters should provide a great interest on account of their reactivities. To our knowledge, Huang reported the aryltellurophosphates were prepared by the free radical reaction initiated by azobisisobutyronitrile (AIBN) or sodium azide (NaN 3 ).…”

Section: Introductionmentioning

confidence: 99%

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Simple and Convenient Method for the Synthesis of Aryltellurophosphates Catalyzed by Cesium Hydroxide

Wang

Liu

et al. 2014

Synthetic Communications

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Simple and Convenient Method for the Synthesis of Aryltellurophosphates Catalyzed by Cesium Hydroxide

Wang

Liu

et al. 2014

Synthetic Communications

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“…Synthesis of 2-[2'-(hydroxyisopropoxyphosphoryl)phenylsulfanyl]benzoic acid (LH 2 ): This trifunctional ligand was synthesized as shown in Scheme 1, by Cu 2 O-catalyzed coupling of diisopropyl 2-sulfanylphenylphosphonate [13,14] with 2-iodobenzoic acid, as reported by Ferretti and Adams, [15] and hydrolysis of the diphenyl sulfide bearing the diisopropylphosphonato group by treatment with sodium azide under the conditions described by Holy. [16] The overall yield of the two steps was 62 %.…”

Section: Resultsmentioning

confidence: 99%

Study of Intramolecular Competition between Carboxylate and Phosphonate for Pt^II with the Aid of a Novel Tridentate Carboxylato‐Thioether‐Phosphonato Ligand

Rizzato¹,

Lecinq²,

Sene³

et al. 2007

Chemistry A European J

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The tridentate dianionic ligand 2-[2'-(hydroxyisopropoxyphosphoryl)phenylsulfanyl]benzoate (L(2-)) reacts with cis-[Pt(NH(3))(2)(H(2)O)(2)](2+) to form an S,O-chelate in which the O-coordinated group is either carboxylate or phosphonate, depending on the degree of protonation of the complex. Carboxylate appears to be the stronger ligand, and the stoichiometric reaction between cis-[Pt(NH(3))(2)(H(2)O)(2)](2+) and L(2-) yields the neutral species [Pt(L)(NH(3))(2)], with L bound by sulfanyl and carboxylate groups, both in solution and in the solid state. Upon protonation of [Pt(L)(NH(3))(2)], the stronger basicity of the carboxylate causes the Pt coordination to switch from carboxylate to phosphonate, and the uncoordinated carboxylate group becomes protonated. In methanolic solution, the first-order kinetics of this rearrangement could be observed by (31)P NMR spectroscopy. Both complexes-the carboxylate-bound neutral complex [Pt(L)(NH(3))(2)].H(2)O (triclinic, P1 (no. 2), a=9.529(6), b=9.766(6), c=12.299(7) angstroms, alpha=106.91(2), beta=101.71(2), gamma=102.05(2) degrees, Z=2) and the perchlorate salt of the phosphonate-bound complex [Pt(LH)(NH(3))(2)]ClO(4).H(2)O (monoclinic, P2(1)/c (no. 14), a=12.095(2), b=14.046(2), c=14.448(2) angstroms, beta=95.55(2) degrees, Z=4)-were characterized by X-ray crystallography.

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“…A few years ago, our group synthesized methacrylates bearing phosphonate groups for potential applications in dental materials 18. These monomers were prepared according to a lithiation‐rearrangement reaction previously developed in the laboratory 19–20…”

Section: Introductionmentioning

confidence: 99%

“…18 These monomers were prepared according to a lithiation-rearrangement reaction previously developed in the laboratory. [19][20] As an extension of this work, we would like to report in this article, the preparation and the photopolymerization of the new aromatic sulfur phosphonic acids 1 and 2 for application in dental materials ( Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photopolymerization of phosphonic acid monomers for applications in compomer materials

Catel

Pluart

Madec

et al. 2010

J of Applied Polymer Sci

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We report here on the characterization of a three‐generation Chinese family with aminoglycoside‐induced and nonsyndromic hearing impairment. Ten of 17 matrilineal relatives exhibited bilateral and sensorineural hearing impairment. Of these, nine matrilineal relatives, who had a history of exposure to aminoglycosides, exhibited variable severity and audiometric configuration of hearing loss. The dose and age at the time of drug administration seemed to be correlated with the severity of the hearing loss experienced by affected individuals. Sequence analysis of the complete mitochondrial genome in the pedigree showed the presence of homoplasmic A1555G mutation and 37 variants belonging to haplogroup D4a. Of those variants, the G7444A mutation is of special interest as the mutation at this position results in a read‐through of the stop condon AGA of the COI message, thereby adding three amino acids (Lys–Gln–Lys) to the C‐terminal of the polypeptide. Alternatively, the G7444A mutation is adjacent to the site of 3′ end endonucleolytic processing of L‐strand RNA precursor, spanning tRNASer(UCN) and ND6 mRNA. Thus, the G7444A mutation, similar to the deafness‐associated A7445G mutation, may lead to a defect in the processing of the L‐strand RNA precursor, thus influencing the phenotypic expression of the A1555G mutation. These data also imply that nuclear background plays a role in the aminoglycoside ototoxicity associated with the A1555G mutation in this Chinese pedigree. © 2005 Wiley‐Liss, Inc.

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Two Methods for the Synthesis of (2-Mercaptophenyl)phosphonic Acid

Cited by 44 publications

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Simple and Convenient Method for the Synthesis of Aryltellurophosphates Catalyzed by Cesium Hydroxide

Simple and Convenient Method for the Synthesis of Aryltellurophosphates Catalyzed by Cesium Hydroxide

Study of Intramolecular Competition between Carboxylate and Phosphonate for Pt^II with the Aid of a Novel Tridentate Carboxylato‐Thioether‐Phosphonato Ligand

Synthesis and photopolymerization of phosphonic acid monomers for applications in compomer materials

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Two Methods for the Synthesis of (2-Mercaptophenyl)phosphonic Acid

Cited by 44 publications

References 0 publications

Simple and Convenient Method for the Synthesis of Aryltellurophosphates Catalyzed by Cesium Hydroxide

Simple and Convenient Method for the Synthesis of Aryltellurophosphates Catalyzed by Cesium Hydroxide

Study of Intramolecular Competition between Carboxylate and Phosphonate for PtII with the Aid of a Novel Tridentate Carboxylato‐Thioether‐Phosphonato Ligand

Synthesis and photopolymerization of phosphonic acid monomers for applications in compomer materials

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Study of Intramolecular Competition between Carboxylate and Phosphonate for Pt^II with the Aid of a Novel Tridentate Carboxylato‐Thioether‐Phosphonato Ligand