- Pd(OAc)2-catalyzed oxidative carbonylation of aromatics: Synthesis of naphthalenecarboxylic acids
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The liquid-phase oxidative carbonylation of aromatics leading to aromatic carboxylic acids is studied to develop new approaches to 2,6- naphthalenedicarboxylic acid (NDA) preparation. It is shown that the catalytic system Pd(OAc)2/K2S2O8 allows the synthesis of naphthalic anhydride (NAn) by direct oxidative carbonylation of naphthalene under mild conditions (25 C, 2 atm CO). The subsequent alkaline hydrolysis of NAn and isomerization of the obtained 1,8-naphthalenedicarboxylic acid salt is known to lead to NDA.
- Elman, Alexander R.
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p. 5527 - 5531
(2013/09/23)
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- Optical resolution of dibenzo[a,g]fluorenol via glycosylation
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A simple optical resolution of dibenzo[a,g]fluorenol has been accomplished via borontrifluoride-mediated Ferrier rearrangement reaction. Copyright Taylor & Francis Group, LLC.
- Banik, Bimal K.,Mukhopadhyay, Chhanda,Logan, Curtis R.,Becker, Frederick F.
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p. 3895 - 3900
(2008/03/14)
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- Antitumor dibenzofluorene derivatives
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Dibenzofluorene derivatives having a formula selected from the group consisting of and salts thereof have antitumor activity. At least one of R1-R13in formula (I) or R1-R12in formula (II) is —R14Z. R14is a substituted or unsubstituted amino or amido group having from 1-12 carbon atoms, and Z is a substituted or unsubstituted heterocyclic group having from 1-12 carbon atoms. The remainder of R1-R13in formula (I) or R1-R12in formula (II) are independently selected from the group consisting of hydrogen, hydroxyl, halogen, nitro, substituted or unsubstituted amino or amido groups having from 1-12 carbon atoms, and alkyl groups having 1-12 carbon atoms.
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- A novel catalytic role of molecular iodine in the oxidation of benzylic alcohols: Microwave-assisted reaction
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Molecular iodine was used to catalyse the oxidation of several benzylic alcohols to the corresponding ketones under the microwave-irradiated method, and the role of iodine was explored.
- Mukhopadhyay,Becker,Banik
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- Sodium bismuthate mediated oxidation study of hydrofluorenes
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The product distribution of sodium bismuthate mediated oxidation of several hydrofluorenes was found to depend on the structure of the starting materials and reaction conditions.
- Banik, Bimal K.,Ghatak, Anjan,Mukhopadhyay, Chhanda,Becker, Frederick F.
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p. 108 - 109
(2007/10/03)
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- Benzylic oxidation by sodium bismuthate in acetic acid: A simple method for the synthesis of polycyclic aromatic ketones
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Oxidation of benzylic methylenes in polycyclic systems to the benzylic ketones was carried out with sodium bismuthate in the presence of acetic acid.
- Banik, Bimal K.,Venkatraman,Mukhopadhyay, Chhanda,Becker, Frederick F.
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p. 7247 - 7250
(2007/10/03)
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- Synthesis of Ketone and Alcohol Derivatives of Methylene-Bridged Polyarenes, Potentially New Classes of Active Metabolites of Carcinogenic Hydrocarbons
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Methods for the syntheses of bridge ketone and alcohol derivatives of methylene-bridged polyarenes from the parent hydrocarbons are described.The polyarenes investigated include 4H-cyclopentaphenanthrene (1a), fluorene (2a), 7H-benzofluorene (3a), 4H-cyclopentachrysene (4a), 11H-benzaceanthrylene (5a), 10H-indenopyrene (6a), 11H-dibenzoaceanthrylene (7a), 4H-fluorenoanthracene (8a), and 7H-dibenzofluorene (9a).The bridge ketone derivatives are most efficiently synthesized via treatment of the parent hydrocarbons with n-butyllithium and reaction of the resulting anionic intermediate s with molecular oxygen.The direct formation of ketones rather than the expected hydroperoxides from reaction of the bridge anions with O2 presumably involves intra- or intermolecular abstraction of a proton from the benzylic site of the intermediate by the peroxy anion leading to loss of hydroxide ion with formation of a carbonyl group.Yields are generally high except in the cases of 1a and 4a; the former affords as the principal product a dimeric alcohol arising from reaction of the anion of 1a with the corresponding ketone 1b.The related bridge alcohols are readily obtained in yields of 75-95percent by reduction of the crude products from the preceding oxidations with NaBH4.
- Harvey, Ronald G.,Abu-shqara, Elias,Yang, ChengXi
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p. 6313 - 6317
(2007/10/02)
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- Remote Aromatic Metalation. An Anionic Friedel-Crafts Equivalent for the Regioselective Synthesis of Condensed Fluorenones from Biaryl and m-Teraryl 2-Amides
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Remote metalation (t-BuLi, LDA) of m-teraryl and biaryl amides (Scheme I) constitutes a short and convenient route to a variety of substituted and condensed fluorenones, including aza analogues (Table I) and the natural product, dengibsinin (6a, Scheme II).
- Fu, Jian-min,Zhao, Bao-ping,Sharp, M. J.,Snieckus, V.
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p. 1683 - 1685
(2007/10/02)
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- A New General Synthesis of Polycyclic Aromatic Compounds Based on Enamine Chemistry
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Alkylation of enamines and enamine salts by benzylic and (β-haloethyl)aryl halides, respectively, followed by acidic cyclodehydration and dehydrogenation provides an efficient synthetic approach to a wide range of polycyclic aromatic compounds of diverse structural types.Specific polycyclic hydrocarbons synthesized by this route include benzo- and benzofluorene, 7H-dibenzo-, 13H-dibenzo-, and 13H-dibenzofluorene, 15H-tribenzofluorene, dibenzochrysene, benzopentaphene, indenofluorene, fluorenofluorene, octahydrodibenzanthracene, dibenzanthracene, octahydrodibenzanthracene, dibenzanthracene, picene, benzopicene, 1H-benzaceanthrylene, and 4H-cyclopentachrysene.This method with appropriate modifications appears to be potentially broader in scope than established traditional methods of polycyclic hydrocarbon synthesis.
- Harvey, Ronald G.,Pataki, John,Cortez, Cecilia,Raddo, Pasquale Di,Yang, ChengXi
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p. 1210 - 1217
(2007/10/02)
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