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13 protocols using styrene oxide

1

Synthesis of Bifunctional Porous Catalysts

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Cetyltrimethylammonium bromide (CTAB), tin chloride pentahydrate, 1-propyl amine, 1-butyl amine, propylene oxide and epichlorohydrin were procured from Loba Chemie Pvt. Ltd, India. Ammonium hydroxide (25 wt%), aniline, cyclohexanol and 1-butanol were obtained from Merck Pvt. Ltd, India. Styrene oxide, methanol, 2-methoxy-2-phenylethanol, ethanol, 1-propanol, propylene oxide, cyclohexene oxide, cyclooctane oxide, epichlorohydrin, phenyl acetaldehyde, tetraethylorthosilicate and pluronic P123 were procured from Sigma-aldrich. NH4-beta (SAR, SiO2/Al2O3 = 25) was obtained from Nankai University Catalyst Co., [H+ form of beta (H-beta) was obtained by calcining at 540 °C for 4 h.
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2

Analytical Quantification of Adducts

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All chemicals were ACS grade or higher, purchased from Sigma Aldrich (St Louis, MO): styrene (substrate), styrene oxide (product), styrene glycol (product), benzyl alcohol (internal standard), acetaminophen (substrate), and 2-acetoamidophenol (internal standard). Barium hydroxide, zinc sulfate, 1,4-dioxane, HPLC grade methanol and HPLC grade acetonitrile were purchased from Fisher Scientific, Wilmington, MA. The acetaminophen-glutathione (APAP-GSH) and acetaminophen-cysteine (APAP-cys) adducts were synthesized in-house. For purification of adducts, solid-phase extraction Oasis MAX columns were obtained from Waters Corp. (Milford, MA). NAPQI solid was provided as a generous gift from Drs. Dean Roberts and Laura James at Arkansas Children’s Hospital (Little Rock, AR).
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3

Synthesis of Pyrazole Derivatives

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EXAMPLE 1

This Example illustrates a method of synthesizing compounds of formulae (I) and (II) in accordance with an embodiment of the present invention.

General Chemistry Methods. The reactions were performed under positive pressure of nitrogen with oven-dried glassware. Pyrazole and 3,5-dimethylPyrazole were purchased from TCI America. Formaldehyde, acetaldehyde, styrene oxide, N-succinimide, THF, and methanol were purchased from Sigma-Aldrich (St. Louis, Mo.).

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4

Bacterial Biocatalytic Epoxidation of Alkenes

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Kanamycin was purchased from Gibco® (Life Technologies, Glasgow, UK). NAD+ was purchased from Prozomix (Haltwhistle, UK). N-hexadecane was purchased from Alfa Aesar (Haverhill, MA, USA). Ethyl acetate was purchased from Merck (Darmstadt, Germany). Styrene, Styrene oxide, and 4-chloroStyrene oxide were purchased from Sigma Aldrich (St. Louis, MO, USA). 4-chloroStyrene was purchased from Carbosynth (San Diego, CA, USA). Other alkenes and standards of epoxides were provided by the Department of Organic Chemistry of the Slovak University of Technology.
Lysogeny broth (LB) was prepared according to [35 ]. Semidefined medium contained 90 g/L glycerol, 10 g/L tryptone, 5 g/L (NH4)2SO4, 3.64 g/L NaH2PO4.2H2O, 4.53 g/L K2HPO4, 4 g/L citric acid, 1% (v/v) trace element solution, 1 g/L MgSO4, 7H2O. Mineral M9 medium contained 5 g/L glycerol, 0.5 g/L MgSO4.7H2O, 0.11 g/L CaCl2, 0.01 g/L thiamine-HCl, and 5% (v/v) M9 salts (85 g/L Na2HPO4.12H2O, 15 g/L KH2PO4, 2.5 g/L NaCl, 5 g/L NH4Cl). All media were supplemented with Kanamycin to a final concentration of 30 µg/mL.
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5

Synthesis of Organosilicon Compounds

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N,N′-Bis(2-hydroxyethyl)-N,N′-bis(trimethoxysilylpropyl)ethylenediamine – BHBPD (66–68% in methanol) was purchased from Gelest. Chromatography grade silica gel mesh 230–400 (hereafter referred to as SiL), 2-iodoethanol (99%), ammonium iodide (99.5%), P123 (average Mn ∼ 5800), tetraethyl orthosilicate – TEOS (98%), 3-chloropropyltrimethoxysilane – 3CPTS (97%), styrene oxide (97%), propylene oxide – PO (99%), 1,2-epoxybutane – 1,2-EB (99%), epichlorohydrin (99%), cyclohexene oxide – CHO (98%), 3-glycidoxypropyltrimethoxysilane (GPS), triethylamine – TEA (99%) and KCl (99%) were purchased from Sigma Aldrich. Ethyl acetate (99.9%), diethyl ether – Et2O (99.8%), ethanol (99%), methanol (99%), hydrochloric acid (37%) and toluene (99%) were obtained from Fischer. P-10 and Q-10 mesoporous silica supports were donated by Fuji Silysia Chemical Ltd. Chloroform-D was obtained from Cambridge Isotope Laboratories. All chemicals were used as obtained with no further purification. Carbon dioxide (99.998%) was obtained from Linde AG.
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6

Styrene oxide synthesis and characterization

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All chemicals and some solvents were purchased from Sigma-Aldrich® (St. Louis, MO, USA) and used as received, in particular styrene oxide (97% purity), imidazole (99% purity) and ZnI2 (98% purity). Carbon dioxide (99.995 % purity) was supplied by Air Liquide. 1H NMR spectra in CDCl3 were acquired on a Bruker Ascend™ 400 spectrometer (Bruker Corporation®, Billerica, MA, USA) at 298 K and referenced to the solvent signals.
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7

Chemical Reagents and Enzymes Protocol

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Styrene, Styrene oxide, phenyl vinyl sulfide, phenyl vinyl sulfoxide, and cofactors were purchased from Sigma-Aldrich (Steinheim, Germany) and Carl Roth (Karlsruhe, Germany). Restriction enzymes were received from MBI Fermentas (St. Leon-Rot, Germany) and New England Biolabs GmbH (Frankfurt am Main, Germany). Oligonucleotides and synthetic genes were synthesized by Eurofins MWG Operon (Ebersberg, Germany).
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8

Synthesis and Characterization of Copper-Iron Nanocomposites

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Copper nitrate trihydrate (Cu(NO3)2·3H2O), iron nitrate nonahydrate (Fe(NO3)3·9H2O), sodium nitrate (NaNO3), 30% H2O2 solution and potassium permanganate (KMnO4) were purchased from Merck, India. Sulphuric acid (H2SO4), sodium hydroxide (NaOH), and 4-nitrophenol (4-NP) were purchased from Fisher Scientific. Styrene, Styrene oxide, tert-butyl hydroperoxide (TBHP in 5–6 M decane), acetonitrile, sodium borohydride (NaBH4), polyvinylidene difluoride (PVDF), acetylene black (SA 75 m2 g−1, bulk density 170–230 g L−1), N-methyl-2-pyrrolidinone (NMP) and graphite powder (mean particle size of <20 μm) were bought from Sigma Aldrich. All the chemicals were used without further purification. Distilled water was used throughout the experiment.
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9

Synthesis of Nanomaterials Using Diverse Chemicals

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Acetone, hydrazine hydrated (N2H4·H2O), polyvinylpyrrolidone (PVP), sodium hydroxide (NaOH), sodium nitrate, sulphuric acid (H2SO4), hydrochloric acid (HCl), sodium nitrate (NaNO3), 4-nitrophenol (4-NP), and nickel(ii)nitrate hexahydrate (Ni(NO3)2·6H2O) were purchased from Fischer Scientific. Silver nitrate (AgNO3), potassium permanganate (KMnO4), sodium azide (NaN3), 30% H2O2 solution, ethylene glycol, acetonitrile, methanol, dichloromethane, toluene, chloroform, diethylamine, and aniline were purchased from Merck, India. Sodium borohydride (NaBH4), aldehydes, piperidine, phenylacetylene, styrene, styrene oxide, cyclohexene oxide, epichlorohydrin, tert-butyl hydroperoxide (TBHP in 5–6 M decane), and graphite powder (mean particle size of <20 mm) were purchased from Sigma-Aldrich. All the chemicals were used without further purification. Distilled water was used throughout the experiment.
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10

Synthesis and Characterization of Picket Fence Iron Porphyrin

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All
reagents were of the
highest grade commercially available and were used without further
purification. Octanethiol (C8SH), butanethiol (C4SH), potassium hexafluorophosphate (KPF6), benzyl alcohol,
benzaldehyde, styrene, styrene oxide, adamantane, and phenylacetaldehyde
were purchased from Sigma-Aldrich. Disodium hydrogen phosphate dihydrate
(Na2HPO4·2H2O), cyclohexane,
and cyclohexanol were purchased from Merck. Triethylamine (Et3N), toluene, ethylbenzene, and acetophenone were purchased
from Spectrochem India Ltd. Au wafers were purchased from Platypus
Technologies (1000 Å of Au on 50 Å of Ti adhesion layer
on top of a Si(III) surface). The picket fence iron porphyrin was
synthesized and characterized following past literature reports.97 (link)
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