Cis 1 2 cyclohexanediol

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.

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)].