Cyclohexene oxide → HCID 86732645, compound

Participants

Reaction Steps

All low pressure catalytic reactions were carried out in magnetically stirred Schlenk tubes, using standard Schlenk techniques. The Schlenk tubes were dried, in an oven at 140° C., for 20 h before any use. In a typical reaction cyclohexene oxide (2.5 mL, 24.7 mmol), and the catalyst were added to a Schlenk tube. The cyclohexene oxide was rapidly de-gassed, before being left stirring under 1 atm CO2 (continuously fed using a reserve cylinder), at 80° C., for 24 h. At the end of the reaction the crude reaction mixture was then taken up in CH2Cl2 and a 0.2 mL of a 5% solution of HCl/MeOH was added. The solution was evaporated in air, after which the product was dried, in vacuo, overnight. No further purification of the product was undertaken as the vacuum was sufficient to remove unreacted cyclohexene oxide. Selectivity was determined by normalisation of the integrals of the methylene protons resonances in the 1H NMR spectra, including the copolymer carbonate linkages (broad signal δ=4.65 ppm), copolymer ether linkages (broad signal δ=3.45 ppm), and cyclic carbonate (multiplets: δ=3.9 ppm (trans-CHC) or 4.63 ppm (cis-CHC)). Conversion was calculated as [(mass of the isolated product weight of the catalyst)/142.1]/moles of starting CHO. Turn-over-number (TON) was calculated as conversion/moles catalyst. Turn-over-frequency (TOF) was calculated as TON/time of reaction (in h).

Provenance & Evidence