Synthesis and Solid-State Structure of (4-Hydroxy-3,5-diiodophenyl)phosphine Oxides. Dimeric Motifs with the Assistance of O-H···O=P Hydrogen Bonds

Bewick, Nicholas; Arendt, Agata; Li, Yan; Szafert, Sławomir; Lis, Tadeusz; Wheeler, Kraig A.; Young, Jonathon; Dembiński, Roman

doi:10.2174/1385272819666141231000247

Cited by 19 publications

(11 citation statements)

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“…Two X‐ray structures of the di(hydroperoxy)propane adducts 1 and 2 , incorporating hydrogen bonds, have been communicated . Recently, hydrogen bonding between P=O and the OH groups of a phenol moiety has successfully been applied to create novel dimeric motifs …”

Section: Resultsmentioning

confidence: 99%

Di(hydroperoxy)alkane Adducts of Phosphine Oxides: Safe, Solid, Stoichiometric, and Soluble Oxidizing Agents

Ahn

Bhuvanesh

Blümel

2017

Chemistry A European J

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The di(hydroperoxy)alkane adducts of phosphine oxides 1-9, Ph PO⋅(HOO) CMe , Cy PO⋅(HOO) CMe , Ph PO⋅ (HOO) CMeEt, Cy PO⋅(HOO) CMeEt, Cy PO⋅(HOO) CEt , Cy PO⋅ (HOO) C(CH ) , Cy PO⋅(HOO) CMePh, (Ph P(O)CH CH P(O)Ph )⋅ ((HOO) CEt ) , and Ph P(O)CH P(O)Ph ⋅(HOO) CMe , respectively, are synthesized and fully characterized by H, C, and P NMR, and IR spectroscopies. Single crystal X-ray structures are reported for 3-9. Different one-pot synthetic pathways, starting from R P, R PO, R PO⋅H O, and R PO⋅H O are explored and discussed and a mechanism for the formation of the di(hydroperoxy)alkane adducts of phosphine oxides is suggested. The longevity of the adducts is tested by monitoring the oxidation of Ph P with quantitative NMR. The solubilities of the adducts in organic solvents are presented, and their applicability as stoichiometric oxidizing agents for the selective oxidation of sulfides to sulfoxides is reported.

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Section: Resultsmentioning

confidence: 99%

Di(hydroperoxy)alkane Adducts of Phosphine Oxides: Safe, Solid, Stoichiometric, and Soluble Oxidizing Agents

Ahn

Bhuvanesh

Blümel

2017

Chemistry A European J

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“…24 The tendency of PO groups to form hydrogen bonds to H 2 O 2 molecules,10 H 2 O, and silanols25 has been described. Recently, hydrogen bonding between PO and phenol OH groups has also been used to create dimeric motifs 26…”

Section: Methodsmentioning

confidence: 99%

“…Recently,h ydrogen bonding between P=Oa nd phenol OH groups has also been used to create dimeric motifs. [26] Tr iarylphosphine oxide adducts differ in structure to that of 1,and they can even lead to different adduct structures and stoichiometries for one given triarylphosphine oxide.F or example,anadduct of Ph 3 PO has been described earlier and its composition has been determined as (Ph 3 PO) 2 ·H 2 O 2 with H 2 O 2 bridging two Ph 3 PO molecules. [27] Our attempt to reproduce this result led to the formation of the new adduct [Ph 3 PO·H 2 O 2 ] 2 ·H 2 O 2 (2;F igure 2).…”

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confidence: 99%

Hydrogen Peroxide and Di(hydroperoxy)propane Adducts of Phosphine Oxides as Stoichiometric and Soluble Oxidizing Agents

et al. 2015

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Aqueous hydrogen peroxide is widely used as an oxidizing agent in industry and academia. Herein, the hydrogen peroxide adducts of phosphine oxides, [tBu3PO⋅H2O2]2 and [Ph3PO⋅H2O2]2⋅H2O2, are described. Additionally, the corresponding di(hydroperoxy)propane adducts R3PO⋅(HOO)2CMe2 (R=Cy, Ph) were synthesized and characterized. All adducts could be obtained as large single crystals suitable for structural characterization by X-ray crystallography and solid-state NMR spectroscopy. The di(hydroperoxy)propane adducts are soluble in organic solvents which enables oxidation reactions in one phase. As the adducts are solid and molecular, they can easily be applied stoichiometrically. No loss of oxidizing power occurs upon long-term storage of the single crystals at room temperature or the powders at -20 °C.

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“…Phosphine oxides form stable hydrogen bonds with diverse types of donors. Examples include phenols, which can be used to create extended assemblies of interest in materials science, as well as naphthol, sulfonic acids, and water . The ability of phosphine oxides to form hydrogen bonds with silanols, phenols, and even chloroform has recently been illustrated .…”

Section: Introductionmentioning

confidence: 99%

Structures and Dynamics of Secondary and Tertiary Alkylphosphine Oxides Adsorbed on Silica

Kharel

Cluff

Bhuvanesh

et al. 2019

Chemistry An Asian Journal

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The three secondary phosphine oxides[ CH 2 = CH(CH 2 ) 4 ] 2 HPO (1), [CH 2 = CH(CH 2 ) 5 ] 2 HPO (2), and [CH 2 = CH(CH 2 ) 6 ] 2 HPO (3), and two diphosphine dioxides, {[CH 2 = CH(CH 2 ) 6 ] 2 PO(CH 2 ) 7 } 2 (4)a nd {[CH 2 = CH(CH 2 ) 6 ] 2 PO(CH 2 ) 4 } 2 (5), incorporating long methylene chains, are described. The single crystal X-ray structures of 1, 2,a nd 5 have been determined. The phosphine oxides 3, 4,a nd 5 have been ad-sorbedo ns ilica in submonolayer quantities to give 3a-5a. The 1 H, 13 C, and 31 Ps olid-state NMRs pectra of polycrystalline 3-5 have been analyzeda nd compared with those of 3a-5a.T he changes of the solid-state NMR characteristics upon adsorption and the surfacem obilities of the phosphine oxides are discussed.[a] Dr.

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Synthesis and Solid-State Structure of (4-Hydroxy-3,5-diiodophenyl)phosphine Oxides. Dimeric Motifs with the Assistance of O-H···O=P Hydrogen Bonds

Cited by 19 publications

References 0 publications

Di(hydroperoxy)alkane Adducts of Phosphine Oxides: Safe, Solid, Stoichiometric, and Soluble Oxidizing Agents

Di(hydroperoxy)alkane Adducts of Phosphine Oxides: Safe, Solid, Stoichiometric, and Soluble Oxidizing Agents

Hydrogen Peroxide and Di(hydroperoxy)propane Adducts of Phosphine Oxides as Stoichiometric and Soluble Oxidizing Agents

Structures and Dynamics of Secondary and Tertiary Alkylphosphine Oxides Adsorbed on Silica

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