High-connectivity networks: characterization of the first uninodal 9-connected net and two topologically novel 7-connected nets

J. Jacob Morris, Bruce C. Noll, Kenneth W. Henderson
2007 Chemical Communications  
General Methods All experimental manipulations were performed under a dry nitrogen atmosphere using standard Schlenk techniques, or in an argon-filled glovebox. 1 All glassware was flamedried under vacuum before use. Hexane was dried immediately before use by passage through columns of copper-based catalyst and alumina (Innovative Technology), and stored over 4 Å molecular sieves. 1,4-Dioxane (diox) was distilled over sodium benzophenone prior to use. [RbOBu t ·Bu t OH] ∞ and RbHMDS (HMDS =
more » ... RbHMDS (HMDS = hexamethyldisilazide) were prepared by literature methods. 2,3 KHMDS was purchased from Aldrich and used as received. 4-Cl-2,6-Dimethylphenol and 2,4,6-trimethylphenol were purchased from Aldrich and were recrystallized from hexane. 2-Pr i -phenol was distilled over CaH 2 and stored over 4 Å molecular sieves. Deuterated solvents were purchased from Cambridge Isotope Laboratories and were dried by storage over 4 Å molecular sieves. 1 H and 13 C NMR spectra were recorded on either a Varian Unity Plus 300 MHz or a Bruker AVANCE DPX-400 spectrometer at 293 K, and were referenced internally to the residual signals of the deuterated solvents. Synthesis of [4-Cl-2,6-Me 2 -C 6 H 2 OK) 2 ·(diox) 3.5 ] ∞ , 1: KHMDS (5 mmol, 1.0 g) was added to a stirred solution of 4-Cl-2,6-dimethylphenol (5 mmol, 0.78 g) in dioxane (10 mL) to give a white precipitate. Complete dissolution was achieved by dilution with dioxane (20 mL) and heating the solution to reflux temperature. X-ray quality crystals were obtained by slowly cooling the resulting solution in a hot water bath. Crystalline yield: 582 mg, 55.6 %. δ H (d 6 -DMSO, 293K) 1.86 (s, 6H, o-Me), 3.57 (s, 14H, CH 2 , dioxane), 6.50 (s, 2H, m-H). δ c (d 6 -DMSO, 293K) 18.31 (o-Me), 66.37 (CH 2 , dioxane), 124.77 (o-C, Ph), 125.87 (m-C, Ph).
doi:10.1039/b711668c pmid:18060138 fatcat:lvv54qmzincddihxhodgwhpige