Malonyl chloride

Chemicals and reagents. Levoglucosenone was graciously provided by Circa group. Citronellol (Sigma Aldrich, Saint-Louis, MO, USA), diisobutylaluminum hydride (DIBAL-H) (Acros, Geel, Belgium), malonyl chloride 97% (Sigma Aldrich), succinyl chloride 95% (Sigma Aldrich), adipoyl chloride 98% (Sigma Aldrich), glutaryl chloride 97% (Sigma Aldrich), Lipopan^® 50 BG (Novozymes, Bagsværd, Denmark) a purified lipase from Thermomyces lanuginosus expressed in Aspergillus oryzae, were used as received. NMR solvents, including CDCl₃ and DMSO-d₆, were purchased from Cambridge Isotopes Laboratories. HPLC grade solvents were purchased from Thermofisher Scientific, Waltham, MA, USA, and used as received. Ultra-pure laboratory-grade water was obtained from MilliQ, 18.2 megaOhms. TLC analyses were performed on an aluminum strip coated with Silica Gel 60 F254 from Merck, revealed under UV-light (254 nm), then in the presence of potassium permanganate staining solution. All manipulations with air-sensitive chemicals and reagents were performed using standard Schlenk techniques on a dual-manifold line, on a high-vacuum line.

C₆₀ fullerene, 8-bromo-1-octanol, malonyl chloride, 4-hydroxy-TEMPO, iodine, 9,10-dimethylanthracene (DMA), tetrabromomethane, benzyl alcohol, 4-methoxybenzyl alcohol, cyclohexanol, allyl alcohol, diphenylmethanol, 1-phenylethanol, toluene, and n-hexane were purchased from Sigma-Aldrich. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU), ethyl malonyl chloride, potassium thioacetate, silica gel 70–230 mesh, and gold powder spherical 0.5–0.8 μm S.A. 0.45–0.7 m²/g were obtained from Alfa Aesar. Sodium sulfate, acetonitrile, triethylamine, methylene chloride, dimethylformamide, and ethyl acetate were purchased from POCh (Poland). Methylene chloride, dimethylformamide, and toluene were dried and purified before use according to standard procedures. Other solvents were HPLC or analytical grade reagents and were used as received.