Hydrogen Peroxide and Di(hydroperoxy)propane Adducts of Phosphine Oxides as Stoichiometric and Soluble Oxidizing Agents
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 syn...
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| Veröffentlicht in: | Angewandte Chemie 2015-11, Vol.127 (45), p.13539-13543 |
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| creator | Ahn, Shin Hye Cluff, Kyle J. Bhuvanesh, Nattamai Blümel, Janet |
| description | 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.
Oxidantien aus dem Regal: Di(hydroperoxy)propan‐Addukte von Phosphanoxiden, [R3PO(HOO)2CMe2] (R=Alkyl, Aryl), wurden in Form sehr großer Einkristalle erhalten. Trotz ihres Oxidationsvermögens sind sie langzeitstabil und außerdem gut löslich in organischen Lösungsmitteln. Damit sind sie ideale Oxidationsmittel für den stöchiometrischen Einsatz in nichtwässrigen Medien. |
| doi_str_mv | 10.1002/ange.201505291 |
| format | Article |
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Oxidantien aus dem Regal: Di(hydroperoxy)propan‐Addukte von Phosphanoxiden, [R3PO(HOO)2CMe2] (R=Alkyl, Aryl), wurden in Form sehr großer Einkristalle erhalten. Trotz ihres Oxidationsvermögens sind sie langzeitstabil und außerdem gut löslich in organischen Lösungsmitteln. Damit sind sie ideale Oxidationsmittel für den stöchiometrischen Einsatz in nichtwässrigen Medien.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201505291</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Adducts ; Chemistry ; Crystal structure ; Crystallography ; Crystals ; Hydrogen ; Hydrogen peroxide ; Hydrogen storage ; Magnetic resonance spectroscopy ; NMR spectroscopy ; Organic solvents ; Oxidation ; Oxidationsmittel ; Oxides ; Oxidizing agents ; P-Liganden ; Phosphanoxide ; Phosphine ; Phosphine oxide ; Propane ; Single crystals ; Solvents ; Structural analysis ; Strukturaufklärung ; Wasserstoffperoxid</subject><ispartof>Angewandte Chemie, 2015-11, Vol.127 (45), p.13539-13543</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright Wiley Subscription Services, Inc. Nov 2015</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3271-b0437d45ccf119833ef21b531343d3519fa9b76a97201baaedf095b2816d6f183</citedby><cites>FETCH-LOGICAL-c3271-b0437d45ccf119833ef21b531343d3519fa9b76a97201baaedf095b2816d6f183</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fange.201505291$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201505291$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Ahn, Shin Hye</creatorcontrib><creatorcontrib>Cluff, Kyle J.</creatorcontrib><creatorcontrib>Bhuvanesh, Nattamai</creatorcontrib><creatorcontrib>Blümel, Janet</creatorcontrib><title>Hydrogen Peroxide and Di(hydroperoxy)propane Adducts of Phosphine Oxides as Stoichiometric and Soluble Oxidizing Agents</title><title>Angewandte Chemie</title><addtitle>Angew. Chem</addtitle><description>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.
Oxidantien aus dem Regal: Di(hydroperoxy)propan‐Addukte von Phosphanoxiden, [R3PO(HOO)2CMe2] (R=Alkyl, Aryl), wurden in Form sehr großer Einkristalle erhalten. Trotz ihres Oxidationsvermögens sind sie langzeitstabil und außerdem gut löslich in organischen Lösungsmitteln. Damit sind sie ideale Oxidationsmittel für den stöchiometrischen Einsatz in nichtwässrigen Medien.</description><subject>Adducts</subject><subject>Chemistry</subject><subject>Crystal structure</subject><subject>Crystallography</subject><subject>Crystals</subject><subject>Hydrogen</subject><subject>Hydrogen peroxide</subject><subject>Hydrogen storage</subject><subject>Magnetic resonance spectroscopy</subject><subject>NMR spectroscopy</subject><subject>Organic solvents</subject><subject>Oxidation</subject><subject>Oxidationsmittel</subject><subject>Oxides</subject><subject>Oxidizing agents</subject><subject>P-Liganden</subject><subject>Phosphanoxide</subject><subject>Phosphine</subject><subject>Phosphine oxide</subject><subject>Propane</subject><subject>Single crystals</subject><subject>Solvents</subject><subject>Structural analysis</subject><subject>Strukturaufklärung</subject><subject>Wasserstoffperoxid</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkU1v3CAQhlGVSt2kvfaMlEt68JYBY8xxm49N1TSJlFQ9ImzwLonXbMBWsvn1wXUVVT20J9DwPDOMXoQ-ApkDIfSz7lZ2TglwwqmEN2gGnELGBBd7aEZInmclzeU7tB_jHSGkoELO0OP5zgS_sh2-tsE_OWOx7gw-cUfr8WE7FneftummO4sXxgx1H7Fv8PXax-3apeLVaEWsI77pvavXzm9sH1z9q9GNb4eqnSD37LoVXqRhfXyP3ja6jfbD7_MA_Tg7vT0-zy6ull-PFxdZzaiArCI5Eybndd0AyJIx21CoOAOWM8M4yEbLShRairR4pbU1DZG8oiUUpmigZAfoaOqbVngYbOzVxsXatm1axw9RgRCECsZlntDDv9A7P4Qu_U5RSgoGQlLyLwoELUrCoKSJmk9UHXyMwTZqG9xGh50Cosa01JiWek0rCXISHl1rd_-h1eJyefqnm02ui719enV1uFeFSPmrn5dLJUv-JRffb9U39gJU4KdT</recordid><startdate>20151102</startdate><enddate>20151102</enddate><creator>Ahn, Shin Hye</creator><creator>Cluff, Kyle J.</creator><creator>Bhuvanesh, Nattamai</creator><creator>Blümel, Janet</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20151102</creationdate><title>Hydrogen Peroxide and Di(hydroperoxy)propane Adducts of Phosphine Oxides as Stoichiometric and Soluble Oxidizing Agents</title><author>Ahn, Shin Hye ; Cluff, Kyle J. ; Bhuvanesh, Nattamai ; Blümel, Janet</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3271-b0437d45ccf119833ef21b531343d3519fa9b76a97201baaedf095b2816d6f183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Adducts</topic><topic>Chemistry</topic><topic>Crystal structure</topic><topic>Crystallography</topic><topic>Crystals</topic><topic>Hydrogen</topic><topic>Hydrogen peroxide</topic><topic>Hydrogen storage</topic><topic>Magnetic resonance spectroscopy</topic><topic>NMR spectroscopy</topic><topic>Organic solvents</topic><topic>Oxidation</topic><topic>Oxidationsmittel</topic><topic>Oxides</topic><topic>Oxidizing agents</topic><topic>P-Liganden</topic><topic>Phosphanoxide</topic><topic>Phosphine</topic><topic>Phosphine oxide</topic><topic>Propane</topic><topic>Single crystals</topic><topic>Solvents</topic><topic>Structural analysis</topic><topic>Strukturaufklärung</topic><topic>Wasserstoffperoxid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ahn, Shin Hye</creatorcontrib><creatorcontrib>Cluff, Kyle J.</creatorcontrib><creatorcontrib>Bhuvanesh, Nattamai</creatorcontrib><creatorcontrib>Blümel, Janet</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ahn, Shin Hye</au><au>Cluff, Kyle J.</au><au>Bhuvanesh, Nattamai</au><au>Blümel, Janet</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hydrogen Peroxide and Di(hydroperoxy)propane Adducts of Phosphine Oxides as Stoichiometric and Soluble Oxidizing Agents</atitle><jtitle>Angewandte Chemie</jtitle><addtitle>Angew. Chem</addtitle><date>2015-11-02</date><risdate>2015</risdate><volume>127</volume><issue>45</issue><spage>13539</spage><epage>13543</epage><pages>13539-13543</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>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.
Oxidantien aus dem Regal: Di(hydroperoxy)propan‐Addukte von Phosphanoxiden, [R3PO(HOO)2CMe2] (R=Alkyl, Aryl), wurden in Form sehr großer Einkristalle erhalten. Trotz ihres Oxidationsvermögens sind sie langzeitstabil und außerdem gut löslich in organischen Lösungsmitteln. Damit sind sie ideale Oxidationsmittel für den stöchiometrischen Einsatz in nichtwässrigen Medien.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ange.201505291</doi><tpages>5</tpages></addata></record> |
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| subjects | Adducts Chemistry Crystal structure Crystallography Crystals Hydrogen Hydrogen peroxide Hydrogen storage Magnetic resonance spectroscopy NMR spectroscopy Organic solvents Oxidation Oxidationsmittel Oxides Oxidizing agents P-Liganden Phosphanoxide Phosphine Phosphine oxide Propane Single crystals Solvents Structural analysis Strukturaufklärung Wasserstoffperoxid |
| title | Hydrogen Peroxide and Di(hydroperoxy)propane Adducts of Phosphine Oxides as Stoichiometric and Soluble Oxidizing Agents |
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