Cyclohexene oxide

Toluene was predried over sodium wire and distilled under nitrogen from sodium. Deuterated solvents were stored over activated 4 Å molecular sieves and degassed by several freeze-thaw cycles. The synthesis of ligand precursors and zinc complexes was carried out as previously reported [53 (link),54 (link),55 (link)]. Cyclohexene oxide (Sigma-Aldrich, Munich, Germany) was pre-dried over calcium hydride, distilled under vacuum and stored under nitrogen in a glove box. Phthalic, maleic and succinic anhydride (Sigma-Aldrich) were sublimed three times and naphthalic anhydride was recrystallized in chloroform and stored under nitrogen in a glove box. All other reagents were purchased from common commercial sources and used as received.

All manipulations were carried out under air. Distilled water was used directly from a Milli-Q purification system (Millipore, Burlington, MA, USA). Acetonitrile, ethanol, methanol and diethyl ether (synthesis grade, Aldrich, St. Louis, MI, USA) were used as solvents and employed as received. Tetraethyl orthosilicate (TEOS, 98% Aldrich), ammonium hydroxide solution (25%, Aldrich), 3-aminopropyltriethoxysilane (APTES, 99%, Aldrich), cis-cyclooctene (CO, 95%, Alfa Aesar, Ward Hill, MA, USA), cyclooctene oxide (COE, 99%, Aldrich), cyclohexene (CH, 99%, Acros, Geel, Belgium), cyclohexene oxide (CHO, 98%, Aldrich), 2-cyclohexen-1-ol (CHol, 95%, TCI, Tokyo, Japan), 2-cyclohexen-1-one (CHone, 96%, TCI), cis-1,2-cyclohexanediol (CHD, 99%, Acros), limonene (Lim, 98%, Aldrich), limonene oxide (LO cis/trans mixture, 97%, Aldrich), (1S, 2S, 4R)-(+)-limonene-1,2-diol (ax-LD, 97%, Aldrich), L-carveol (C^olcis/trans mixture, 95%, Aldrich), (R)-(-) Carvone (C^one 98%, Aldrich), cyclohexanol (CYol, 99%, Alfa Aesar, Karlsruhe, Germany), cyclohexanone (CYone, 99.8%, Acros), phosphotungstic acid hydrate (reagent grade, Aldrich), molybdatophosphoric acid hydrate (reagent grade, Merck, Darmstadt, Germany) and TBHP (70% in water, Aldrich) were used as received. The pure cis-LO, trans-LO and eq-LD were synthesized according to literature procedures [58 (link),59 (link),60 (link)].

Styrene oxide (C₈H₈O, 97%), cyclohexene oxide (C₆H₁₀O, 98%), aniline (C₆H₇N, 99%), and trimesic acid (C₉H₆O₆, 95%) were acquired from Aldrich. The phosphomolybdic acid hydrate (H₃PMo₁₂O₄₀.xH₂O) was acquired from Sigma-Aldrich. Formic acid (CH₂O₂, 90%) and dimethylformamide (C₃H₇NO, ≥99.5%) were acquired from Fisher. Acetonitrile (CH₃CN, 99.5%, MeCN), acetone (C3H6O, 99.8%), and mEthanol (CH₄O, ≥99.9%) were purchased from Carlo Erba. Zirconium chloride (ZrCl₄, 99.5%) was acquired from Alfa Aesar. Ethanol (C₂H₆O, ≥99.8%) and acetic acid (C₂H₄O₂, ≥99.8%) were purchased from Honeywell. Isopropanol (C₃H₈O) was acquired from Merck Millipore. These chemical compounds used in this research work were used as received, without any type of purification treatment prior to use.

The reagents used for the investigations and syntheses were of the highest purity commercially available and were used without further purification. The solvent for all experiments was acetonitrile (≥99.9%, HPLC grade) purchased from Aldrich. High-purity argon (grade 5.0) supplied by Linde (Poland) was used to de-aerate the solutions. Iron(II) perchlorate, Fe(ClO₄)₂·6H₂O, sodium hydroxide (98%), biphenyl (PhPh, ≥99%), cyclohexene (≥99%), 2-cyclohexen-1-one (95%), 2-cyclohexen-1-ol (95%), cyclohexene oxide (98%), (R)-(+)-limonene (97%), (-)-carveol, mixture of isomers, (97%), (R)-(-)-carvone (98%), (+)-limonene oxide, mixture of cis and trans, (97%), (S)-(-)-perillyl alcohol (96%), (S)-(-)-perillaldehyde (92%), di-2-pyridilketone oxime (98%), 2-picolyl chloride hydrochloride (98%), iodobenzene (98%), and chloroform (98%) were obtained from Aldrich. Peracetic acid (39%) and perchloric acid (70%) were delivered by Fluka. Ammonium acetate (97%), sodium sulfate anhydrous (99%), magnesium sulfate anhydrous (99%), and ammonia solution (25%) were purchased from POCH (Poland). PhIO was synthesized by a well-known procedure [89 ,90 ].

All manipulations were carried out under air. Distilled water was used directly from a Milli-Q purification system (Millipore, Burlington, MA, USA). Acetonitrile, ethanol, methanol (synthesis grade, Aldrich) were used as solvents as received. Tetraethyl orthosilicate (TEOS, 98% Aldrich, St. Louis, MI, USA), ammonium hydroxide solution (25%, Aldrich), 3-(Triethoxysilyl)propionitrile (97%, Aldrich), cis-cyclooctene (95%, Alfa Aesar, Karlsruhe, Germany), cyclooctene oxide (99%, Aldrich), cyclohexene (99%, Acros), cyclohexene oxide (98%, Aldrich), 2-cyclohexen-1-ol (95%, TCI, Tokyo, Japan)), 2-cyclohexen-1-one (96%,TCI), cis-1,2-cyclohexanediol (99%, Acros, Geel, Belgium), cyclohexanol (99%, Alfa Aesar), cyclohexanone (99.8%, Acros) and TBHP (70% in water, Aldrich) were used as received.