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Title: [PhSiO 1.5 ] 8,10,12 as nanoreactors for non-enzymatic introduction of ortho, meta or para-hydroxyl groups to aromatic molecules

Abstract

Traditional electrophilic bromination follows long established “rules”: electron-withdrawing substituents cause bromination selective formetapositions, whereas electron-donating substituents favororthoandparabromination.

Authors:
 [1];  [1];  [2];  [2]; ORCiD logo [1]
  1. Macromolecular Science and Engineering; and Materials Science and Engineering; University of Michigan; Ann Arbor; USA
  2. Department of Polymer Processing; Iran Polymer and Petrochemical Institute; Tehran; Iran
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Center for Solar and Thermal Energy Conversion (CSTEC); Univ. of Michigan, Ann Arbor, MI (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1535219
DOE Contract Number:  
SC0000957
Resource Type:
Journal Article
Journal Name:
Dalton Transactions
Additional Journal Information:
Journal Volume: 46; Journal Issue: 27; Journal ID: ISSN 1477-9226
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
Chemistry

Citation Formats

Bahrami, Mozhgan, Zhang, Xingwen, Ehsani, Morteza, Jahani, Yousef, and Laine, Richard M. [PhSiO 1.5 ] 8,10,12 as nanoreactors for non-enzymatic introduction of ortho, meta or para-hydroxyl groups to aromatic molecules. United States: N. p., 2017. Web. doi:10.1039/c7dt00373k.
Bahrami, Mozhgan, Zhang, Xingwen, Ehsani, Morteza, Jahani, Yousef, & Laine, Richard M. [PhSiO 1.5 ] 8,10,12 as nanoreactors for non-enzymatic introduction of ortho, meta or para-hydroxyl groups to aromatic molecules. United States. doi:10.1039/c7dt00373k.
Bahrami, Mozhgan, Zhang, Xingwen, Ehsani, Morteza, Jahani, Yousef, and Laine, Richard M. Sun . "[PhSiO 1.5 ] 8,10,12 as nanoreactors for non-enzymatic introduction of ortho, meta or para-hydroxyl groups to aromatic molecules". United States. doi:10.1039/c7dt00373k.
@article{osti_1535219,
title = {[PhSiO 1.5 ] 8,10,12 as nanoreactors for non-enzymatic introduction of ortho, meta or para-hydroxyl groups to aromatic molecules},
author = {Bahrami, Mozhgan and Zhang, Xingwen and Ehsani, Morteza and Jahani, Yousef and Laine, Richard M.},
abstractNote = {Traditional electrophilic bromination follows long established “rules”: electron-withdrawing substituents cause bromination selective formetapositions, whereas electron-donating substituents favororthoandparabromination.},
doi = {10.1039/c7dt00373k},
journal = {Dalton Transactions},
issn = {1477-9226},
number = 27,
volume = 46,
place = {United States},
year = {2017},
month = {1}
}

Works referenced in this record:

Structure-antioxidant activity relationships of flavonoids and phenolic acids
journal, January 1996

  • Rice-Evans, Catherine A.; Miller, Nicholas J.; Paganga, George
  • Free Radical Biology and Medicine, Vol. 20, Issue 7
  • DOI: 10.1016/0891-5849(95)02227-9

Oxidation of sulfides to sulfoxides. Part 2: Oxidation by hydrogen peroxide
journal, August 2005


Silafunctional compounds in organic synthesis
journal, July 1984


D 5h [PhSiO 1.5 ] 10 synthesis via F catalyzed rearrangement of [PhSiO 1.5 ] n . An experimental/computational analysis of likely reaction pathways
journal, January 2016

  • Furgal, Joseph C.; Goodson III, Theodore; Laine, Richard M.
  • Dalton Transactions, Vol. 45, Issue 3
  • DOI: 10.1039/C5DT04182A

Mushroom Tyrosinase:  Recent Prospects
journal, May 2003

  • Seo, Sung-Yum; Sharma, Vinay K.; Sharma, Niti
  • Journal of Agricultural and Food Chemistry, Vol. 51, Issue 10
  • DOI: 10.1021/jf020826f

Novel meta -Selective Friedel–Crafts Acylation of Phenylsilsesquioxane
journal, October 2010


Effects of chloride ions on the iron(III)-catalyzed decomposition of hydrogen peroxide and on the efficiency of the Fenton-like oxidation process
journal, June 2006


The Crystal Structure of Catechol Oxidase:  New Insight into the Function of Type-3 Copper Proteins
journal, March 2002

  • Gerdemann, Carsten; Eicken, Christoph; Krebs, Bernt
  • Accounts of Chemical Research, Vol. 35, Issue 3
  • DOI: 10.1021/ar990019a

The effects of Fenton's reagent pretreatment on the biodegradability of nonionic surfactants
journal, August 1999


1-Silyl-2,6-diketones:  Versatile Intermediates for the Divergent Synthesis of Five- and Six-Membered Carbocycles under Radical and Anionic Conditions
journal, August 2006

  • Chiara, Jose L.; García, Ángela; Sesmilo, Esther
  • Organic Letters, Vol. 8, Issue 18
  • DOI: 10.1021/ol0613517

Oxidative Stress Gated by Fenton and Haber Weiss Reactions and Its Association With Alzheimer’s Disease
journal, August 2014

  • Kanti Das, Tushar; Wati, Mas Rina; Fatima-Shad, Kaneez
  • Archives of Neuroscience, Vol. 2, Issue 3
  • DOI: 10.5812/archneurosci.20078

Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds
journal, October 1997

  • Fleming, Ian; Barbero, Asuncion; Walter, David
  • Chemical Reviews, Vol. 97, Issue 6
  • DOI: 10.1021/cr941074u

Enzymatic hydroxylation of aromatic compounds
journal, April 1956

  • Mitoma, Chozo; Posner, Herbert S.; Reitz, Henry C.
  • Archives of Biochemistry and Biophysics, Vol. 61, Issue 2
  • DOI: 10.1016/0003-9861(56)90366-6

Spherical, Polyfunctional Molecules Using Poly(bromophenylsilsesquioxane)s as Nanoconstruction Sites
journal, May 2005

  • Brick, C. M.; Tamaki, R.; Kim, S. -G.
  • Macromolecules, Vol. 38, Issue 11
  • DOI: 10.1021/ma0473014

Photoluminescence from silsesquioxanes R8(SiO1.5)8
journal, April 2002


pH Effects on Iron-Catalyzed Oxidation using Fenton’s Reagent
journal, November 2008

  • Duesterberg, Christopher K.; Mylon, Steven E.; Waite, T. David
  • Environmental Science & Technology, Vol. 42, Issue 22
  • DOI: 10.1021/es801720d

Synthesis of Phenols via Fluoride-free Oxidation of Arylsilanes and Arylmethoxysilanes
journal, August 2012

  • Rayment, Elizabeth J.; Summerhill, Nick; Anderson, Edward A.
  • The Journal of Organic Chemistry, Vol. 77, Issue 16
  • DOI: 10.1021/jo301363h

Hydroxylation of Benzene to Phenol under Air and Carbon Monoxide Catalyzed by Molybdovanadophosphoric Acid
journal, April 2005

  • Tani, Masayuki; Sakamoto, Takao; Mita, Shuichi
  • Angewandte Chemie International Edition, Vol. 44, Issue 17
  • DOI: 10.1002/anie.200462769

Eco-friendly, Selective Hydroxylation of C-7 Aromatic Compounds Catalyzed by TS-1/H 2 O 2 System under Solvent-free Solid−Liquid−Liquid-Type Triphase Conditions
journal, December 2007

  • Mukherjee, P.; Bhaumik, Asim; Kumar, Rajiv
  • Industrial & Engineering Chemistry Research, Vol. 46, Issue 25
  • DOI: 10.1021/ie070088q

Tyrosinase: a comprehensive review of its mechanism
journal, February 1995

  • Sánchez-Ferrer, Álvaro; Neptuno Rodríguez-López, José; García-Cánovas, Francisco
  • Biochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology, Vol. 1247, Issue 1
  • DOI: 10.1016/0167-4838(94)00204-T

Iridium-Catalyzed Arene Ortho -Silylation by Formal Hydroxyl-Directed C−H Activation
journal, December 2010

  • Simmons, Eric M.; Hartwig, John F.
  • Journal of the American Chemical Society, Vol. 132, Issue 48
  • DOI: 10.1021/ja1086547

Fungal tyrosinases: new prospects in molecular characteristics, bioengineering and biotechnological applications
journal, February 2006


Removal of COD from olive mill wastewater by Fenton's reagent: Kinetic study
journal, September 2009


Carbon-13-fluorine-19 coupling constants in benzotrifluorides
journal, October 1977

  • Newmark, Richard A.; Hill, James R.
  • Organic Magnetic Resonance, Vol. 9, Issue 10
  • DOI: 10.1002/mrc.1270091008

Electrochemical generation of the Fenton's reagent: application to atrazine degradation
journal, August 2002


Oxidation and Ammoxidation of Aromatics
journal, October 2004

  • Lücke, B.; Narayana, K. V.; Martin, A.
  • Advanced Synthesis & Catalysis, Vol. 346, Issue 12
  • DOI: 10.1002/adsc.200404027

Syntheses of highly-functionalized polyhedral oligosilsesquioxanes
journal, December 1989


The Hydroxylation of Aromatic Compounds by Hydrogen Peroxide in the Presence of Catalytic Amounts of Ferric Ion and Catechol. Product Studies, Mechanism, and Relation to Some Enzymic Reaction 1,2
journal, November 1966

  • Hamilton, Gordon A.; Hanifin, J. William; Friedman, Joel P.
  • Journal of the American Chemical Society, Vol. 88, Issue 22
  • DOI: 10.1021/ja00974a043

The Hydroxylation of Anisole by Hydrogen Peroxide in the Presence of Catalytic Amounts of Ferric Ion and Catechol. Scope, Requirements, and Kinetic Studies 1,2
journal, November 1966

  • Hamilton, Gordon A.; Friedman, Joel P.; Campbell, Patrick M.
  • Journal of the American Chemical Society, Vol. 88, Issue 22
  • DOI: 10.1021/ja00974a042

Influence of Fenton reagent oxidation on mineralization and decolorization of municipal landfill leachate
journal, April 2010

  • Mohajeri, Soraya; Aziz, Hamidi Abdul; Isa, Mohamed Hasnain
  • Journal of Environmental Science and Health, Part A, Vol. 45, Issue 6
  • DOI: 10.1080/10934521003648883

Aromatic intermediate formation during oxidative degradation of Bisphenol A by homogeneous sub-stoichiometric Fenton reaction
journal, May 2010


Silafunctional compounds in organic synthesis. 21. Hydrogen peroxide oxidation of alkenyl(alkoxy)silanes
journal, January 1984


Synthesis of amino-containing oligophenylsilsesquioxanes
journal, May 2005


Influence of Substituents in Fluorobenzene Derivatives on the Cytochrome P450-Catalyzed Hydroxylation at the Adjacent Ortho Aromatic Carbon Center
journal, March 1997

  • Koerts, Janneke; Velraeds, Martine M. C.; Soffers, Ans E. M. F.
  • Chemical Research in Toxicology, Vol. 10, Issue 3
  • DOI: 10.1021/tx960048j

Advanced Oxidation Processes for Organic Contaminant Destruction Based on the Fenton Reaction and Related Chemistry
journal, January 2006

  • Pignatello, Joseph J.; Oliveros, Esther; MacKay, Allison
  • Critical Reviews in Environmental Science and Technology, Vol. 36, Issue 1
  • DOI: 10.1080/10643380500326564

Fleming−Tamao Oxidation and Masked Hydroxyl Functionality:  Total Synthesis of (+)-Pramanicin and Structural Elucidation of the Antifungal Natural Product (−)-Pramanicin
journal, August 1999

  • Barrett, Anthony G. M.; Head, John; Smith, Marie L.
  • The Journal of Organic Chemistry, Vol. 64, Issue 16
  • DOI: 10.1021/jo9905672

A review of classic Fenton’s peroxidation as an advanced oxidation technique
journal, March 2003


Investigations on the selective oxidation of benzonitrile using nitrous oxide catalyzed by modified ZSM-5 zeolites
journal, September 2004


Enzymatic hydroxylation of aromatic compounds
journal, January 2007


Direct catalytic oxidation of benzene to phenol over metal-free graphene-based catalyst
journal, January 2013

  • Yang, Jing-He; Sun, Geng; Gao, Yongjun
  • Energy & Environmental Science, Vol. 6, Issue 3
  • DOI: 10.1039/c3ee23623d

The oxidation of the carbon-silicon bond
journal, May 1996


Fenton-Mediated Oxidation in the Presence and Absence of Oxygen
journal, July 2005

  • Duesterberg, Christopher K.; Cooper, William J.; Waite, T. David
  • Environmental Science & Technology, Vol. 39, Issue 13
  • DOI: 10.1021/es048378a

para -Octaiodophenylsilsesquioxane, [ p -IC 6 H 4 SiO 1.5 ] 8 , a Nearly Perfect Nano-Building Block
journal, January 2008

  • Roll, Mark F.; Asuncion, Michael Z.; Kampf, Jeffrey
  • ACS Nano, Vol. 2, Issue 2
  • DOI: 10.1021/nn700196d

Radical and non-radical chemistry of the Fenton-like systems in the presence of organic substrates
journal, June 2001


Controlling Iron-Catalyzed Oxidation Reactions: From Non-Selective Radical to Selective Non-Radical Reactions
journal, September 2008

  • Shi, Feng; Tse, Man Kin; Li, Zuopeng
  • Chemistry - A European Journal, Vol. 14, Issue 29
  • DOI: 10.1002/chem.200801432

Polyhedral Phenylsilsesquioxanes
journal, March 2011

  • Laine, Richard M.; Roll, Mark F.
  • Macromolecules, Vol. 44, Issue 5
  • DOI: 10.1021/ma102360t

Mechanism of Cytochrome P450-Catalyzed Aromatic Hydroxylation of Estrogens
journal, July 1997

  • Sarabia, Stephen F.; Zhu, Bao Ting; Kurosawa, Takao
  • Chemical Research in Toxicology, Vol. 10, Issue 7
  • DOI: 10.1021/tx970021f

Antioxidant and structure–activity relationships (SARs) of some phenolic and anilines compounds
journal, December 2013