A new synthesis of ortho-Quinones by transition-metal-mediated oxygenation of phenols with tert-butylhydroperoxide and the mimoun oxodiperoxo molybdenum complex [Mo(O2)2O] · Py · HMPT

A new synthesis of ortho-Quinones by transition-metal-mediated oxygenation of phenols with tert-butylhydroperoxide and the mimoun oxodiperoxo molybdenum complex [Mo(O2)2O] · Py · HMPT

A specific oxygenation of phenols to ortho‐quinones can be effected by a combination of the transition metal complexes Ti(OiPr)4, VO(acac)2, Zr(acac)4, Zr(OnPr)4 and tert‐butylhydroperoxide (TBHP) or [Mo(O2)2O] · Py · HMPT. Naphthols, anthracenols, phenanthrols and donor substituted mononuclear phen...

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Veröffentlicht in:Chemische Berichte 1989-12, Vol.122 (12), p.2323-2330
Hauptverfasser: Krohn, Karsten, Rieger, Hagen, Khanbabaee, Karamali
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ortho-Quinones
oxygenation
Phenols
Phenols, oxygenation
tert-Butyl hydroperoxide
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Khanbabaee, Karamali
description A specific oxygenation of phenols to ortho‐quinones can be effected by a combination of the transition metal complexes Ti(OiPr)4, VO(acac)2, Zr(acac)4, Zr(OnPr)4 and tert‐butylhydroperoxide (TBHP) or [Mo(O2)2O] · Py · HMPT. Naphthols, anthracenols, phenanthrols and donor substituted mononuclear phenols are readily converted into the corresponding 1,2‐quinones. Unhindered ortho‐naphthoquinones can yield binaphthyls with unreacted starting material by Michael addition. Eine neue ortho‐Chinon‐Synthese durch Oxygenierung von Phenolen mit den Systemen tert‐Butylhydroperoxid/Übergangsmetall‐Komplex und dem Mimounschen Oxodiperoxo‐Molydbän‐Komplex [Mo(O2)2O] · py · HMPT Phenole können mit einer Kombination der Übergangsmetall‐Komplexe Ti(OiPr)4, VO(acac)2, Zr(acac)4, Zr(OnPr)4 und tert‐Butylhydroperoxid oder mit [Mo(O2)2O] · Py · HMPT spezifisch zu ortho‐Chinonen oxygeniert werden. Naphthole, Anthracenole, Phenanthrole und Donor‐substituierte einkernige Phenole werden glatt in die entsprechenden 1,2‐Chinone übergeführt. Ungehinderte ortho‐Napthochinone können unter Michael‐Addition mit nicht umgesetztem Ausgangsmaterial zu Biarylen abreagieren.
doi_str_mv 10.1002/cber.19891221220
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Naphthols, anthracenols, phenanthrols and donor substituted mononuclear phenols are readily converted into the corresponding 1,2‐quinones. Unhindered ortho‐naphthoquinones can yield binaphthyls with unreacted starting material by Michael addition. Eine neue ortho‐Chinon‐Synthese durch Oxygenierung von Phenolen mit den Systemen tert‐Butylhydroperoxid/Übergangsmetall‐Komplex und dem Mimounschen Oxodiperoxo‐Molydbän‐Komplex [Mo(O2)2O] · py · HMPT Phenole können mit einer Kombination der Übergangsmetall‐Komplexe Ti(OiPr)4, VO(acac)2, Zr(acac)4, Zr(OnPr)4 und tert‐Butylhydroperoxid oder mit [Mo(O2)2O] · Py · HMPT spezifisch zu ortho‐Chinonen oxygeniert werden. Naphthole, Anthracenole, Phenanthrole und Donor‐substituierte einkernige Phenole werden glatt in die entsprechenden 1,2‐Chinone übergeführt. 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Ber</addtitle><description>A specific oxygenation of phenols to ortho‐quinones can be effected by a combination of the transition metal complexes Ti(OiPr)4, VO(acac)2, Zr(acac)4, Zr(OnPr)4 and tert‐butylhydroperoxide (TBHP) or [Mo(O2)2O] · Py · HMPT. Naphthols, anthracenols, phenanthrols and donor substituted mononuclear phenols are readily converted into the corresponding 1,2‐quinones. Unhindered ortho‐naphthoquinones can yield binaphthyls with unreacted starting material by Michael addition. Eine neue ortho‐Chinon‐Synthese durch Oxygenierung von Phenolen mit den Systemen tert‐Butylhydroperoxid/Übergangsmetall‐Komplex und dem Mimounschen Oxodiperoxo‐Molydbän‐Komplex [Mo(O2)2O] · py · HMPT Phenole können mit einer Kombination der Übergangsmetall‐Komplexe Ti(OiPr)4, VO(acac)2, Zr(acac)4, Zr(OnPr)4 und tert‐Butylhydroperoxid oder mit [Mo(O2)2O] · Py · HMPT spezifisch zu ortho‐Chinonen oxygeniert werden. Naphthole, Anthracenole, Phenanthrole und Donor‐substituierte einkernige Phenole werden glatt in die entsprechenden 1,2‐Chinone übergeführt. 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Ber</addtitle><date>1989-12</date><risdate>1989</risdate><volume>122</volume><issue>12</issue><spage>2323</spage><epage>2330</epage><pages>2323-2330</pages><issn>0009-2940</issn><eissn>1099-0682</eissn><abstract>A specific oxygenation of phenols to ortho‐quinones can be effected by a combination of the transition metal complexes Ti(OiPr)4, VO(acac)2, Zr(acac)4, Zr(OnPr)4 and tert‐butylhydroperoxide (TBHP) or [Mo(O2)2O] · Py · HMPT. Naphthols, anthracenols, phenanthrols and donor substituted mononuclear phenols are readily converted into the corresponding 1,2‐quinones. Unhindered ortho‐naphthoquinones can yield binaphthyls with unreacted starting material by Michael addition. Eine neue ortho‐Chinon‐Synthese durch Oxygenierung von Phenolen mit den Systemen tert‐Butylhydroperoxid/Übergangsmetall‐Komplex und dem Mimounschen Oxodiperoxo‐Molydbän‐Komplex [Mo(O2)2O] · py · HMPT Phenole können mit einer Kombination der Übergangsmetall‐Komplexe Ti(OiPr)4, VO(acac)2, Zr(acac)4, Zr(OnPr)4 und tert‐Butylhydroperoxid oder mit [Mo(O2)2O] · Py · HMPT spezifisch zu ortho‐Chinonen oxygeniert werden. Naphthole, Anthracenole, Phenanthrole und Donor‐substituierte einkernige Phenole werden glatt in die entsprechenden 1,2‐Chinone übergeführt. Ungehinderte ortho‐Napthochinone können unter Michael‐Addition mit nicht umgesetztem Ausgangsmaterial zu Biarylen abreagieren.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/cber.19891221220</doi><tpages>8</tpages></addata></record>
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source Wiley Online Library Journals Frontfile Complete
subjects ortho-Quinones
oxygenation
Phenols
Phenols, oxygenation
tert-Butyl hydroperoxide
title A new synthesis of ortho-Quinones by transition-metal-mediated oxygenation of phenols with tert-butylhydroperoxide and the mimoun oxodiperoxo molybdenum complex [Mo(O2)2O] · Py · HMPT
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