stated, all manipulations
of air- and/or moisture-sensitive compounds were carried out in oven-dried
glassware under an atmosphere of N2. All solvents and reagents
were purchased from Alfa Aesar, Spectrum Chemicals, Acros Organics,
TCI America, and Sigma-Aldrich and used as received unless otherwise
noted. Organic solvents were dried by passing through a column of
alumina and were degassed by vigorous bubbling of N2 through
the solvent for 20 min. Flash column chromatography was performed
on SiliCycle silica gel (particle size 40–63 μm). Thin-layer
chromatography was carried out using SiliCycle silica gel 60 Å
F-254 precoated plates (0.25 mm thick) and visualized by UV absorption.
All 1H and 13C NMR spectra were recorded on
a Bruker AV-600 spectrometer and are referenced to residual solvent
peaks (CDCl3, 1H NMR = 7.26 ppm, 13C NMR = 77.16 ppm; CD2Cl2, 1H NMR
= 5.32 ppm, 13C NMR = 53.84 ppm). EI mass spectrometry
was performed on an AutoSpec Premier (Waters) system in positive ionization
mode. MALDI mass spectrometry was performed on a Voyager-DE PRO (Applied
Biosystems Voyager System 6322) instrument in positive mode using
a matrix of dithranol. 10,10′-Dibromo-9,9′-bianthryl
was synthesized following a reported procedure.74 (link)