The facile dealkylation of phosphonic acid dialkyl esters by bromotrimethylsilane

McKenna, Charles E.; Higa, Melvin T.; Cheung, Neil H.; McKenna, M. C.

doi:10.1016/s0040-4039(01)92575-4

Cited by 477 publications

(300 citation statements)

References 10 publications

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“…The formation of an isopropyl phosphonate indicates that, similarly to the reactions of carboxylic acids, esterification of the (noncoordinated or coordinated) phosphonic acid could also be the source of the oxo groups, especially because the ester/μ 3 -O ratio in 2 is 1:1. The reactions of bis(trimethylsilyl) phosphonates with alcohols leads to the corresponding phosphonic acid and alkoxytrimethylsilane [10] in a fast reaction. [11] Use of the trimethylsilyl esters thus allows generation of the phosphonic acid in situ, which may substitute some of the OiPr groups of Ti(OiPr) 4 .…”

Section: Resultsmentioning

confidence: 99%

Influence of the Phosphonate Ligand on the Structure of Phosphonate‐Substituted Titanium Oxo Clusters

2013

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The reaction of titanium isopropoxide, Ti(OiPr)4, with bis(trimethylsilyl) phosphonates has led to structures containingTi3O units [= Ti3(μ3‐O)(μ2‐OiPr)3(OiPr)3(O3PR)3] as the basic structural motif. This unit can be capped by a single Ti(OiPr)2L group (L = neutral ligand) through phosphonate bridges (for R = xylyl), or sandwich‐like structures can be formed with two Ti3O units bonded to a central Ti atom (for R = CH2CH2CH2Cl or benzyl). For R = allyl or ethyl, dimeric clusters were formed in which two Ti4 cluster units are bridged by isopropyl phosphonate ligands. For comparison, Ti(OiPr)4 was also treated with allylphosphonic acid to yield a Ti4 cluster. The reaction of Ti(OiPr)4 with the bulky bis(trimethylsilyl) 2‐naphthylmethyphosphonate did not yield an oxo cluster but instead the phosphonate‐substituted titanium alkoxide Ti4(OiPr)8(O3PCH2naphthyl)4.

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Section: Resultsmentioning

confidence: 99%

Influence of the Phosphonate Ligand on the Structure of Phosphonate‐Substituted Titanium Oxo Clusters

2013

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“…These attempts included (a) reaction with Me,SiCI/KI or NaBr in acetonitrile (7,8), which resulted either in opening of the lactone ring, or very slow reaction giving ill-defined products; (b) reaction with HBr/acetic acid (9), which gave polar products that did not provide starting material upon remethylation; (c) treatment with Lil/2,4,6-collidine in DMF what appeared to be the desired acid or acids, since remethylation provided starting material. However, the purification proved to be extremely difficult, and no clean acid could be isolated; (e) sodium bromide/benzyl triethylammonium chloride ( I 2): the reaction was very slow, and no desired acid could be isolated.…”

Section: Synthesis Of Phosphonolactone 12mentioning

confidence: 99%

“…Altlel~vtle 8 Thc cstcr 7b (1.78 g. 6.75 mmol) was dissolvcd in CH2CI2 and cooled to -78°C. Then ozone was bubblcd through thc solution until it turned blue.…”

Section: ) 178 (4) 160 (4) 108 (8) 107 (3) 91 (100) 79 (4) 65mentioning

confidence: 99%

γ-Phosphono-γ-lactones. The use of allyl esters as easily removable phosphonate protecting groups

Kamber¹,

Just²

1985

Can. J. Chem.

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“…(3, 3-Dimethylbutyl)-phosphonic acid diethylester (4.50 g) was hydrolyzed according to McKenna et al using trimethylbromosilane (6.23 g), affording (3,3-dimethylbutyl)-phosphonic acid (3.36 g, 100 %). [19,20] …”

Section: Experimental Section Materialsmentioning

confidence: 99%

Molecular‐Scale Interface Engineering of Nanocrystalline Titania by Co‐adsorbents for Solar Energy Conversion

et al. 2012

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The use of mixed self‐assembled monolayers, combining hydrophobic co‐adsorbents with the sensitizer, has been demonstrated to enhance the efficiency of dye‐sensitized solar cells (DSCs). Herein, the influence of the anchoring groups of the co‐adsorbents on the performance of the DSCs is carefully examined by selecting two model molecules: neohexyl phosphonic acid (NHOOP) and bis‐(3,3‐dimethyl‐butyl)‐phosphinic acid (DINHOP). The effect of these co‐adsorbents on the photovoltaic performance (J–V curves, incident photon‐to‐electron conversion efficiency) is investigated. Photoelectron spectroscopy and electrochemical impedance spectroscopy are performed to assess the spatial configuration of adsorbed dye and co‐adsorbent molecules. The photoelectron spectroscopy studies indicate that the ligands of the ruthenium complex, containing thiophene groups, point out away from the surface of TiO2 in comparison with the NCS group.

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The facile dealkylation of phosphonic acid dialkyl esters by bromotrimethylsilane

Cited by 477 publications

References 10 publications

Influence of the Phosphonate Ligand on the Structure of Phosphonate‐Substituted Titanium Oxo Clusters

Influence of the Phosphonate Ligand on the Structure of Phosphonate‐Substituted Titanium Oxo Clusters

γ-Phosphono-γ-lactones. The use of allyl esters as easily removable phosphonate protecting groups

Molecular‐Scale Interface Engineering of Nanocrystalline Titania by Co‐adsorbents for Solar Energy Conversion

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