Mercury plus 400 spectrometer

Reaction conditions and
yields were not optimized.
Anhydrous solvents were purchased from Aldrich and were used without
further purification. All other chemicals and reagents were purchased
from Sigma-Aldrich Co. LLC, Combi-Blocks, TCI America, OChem Incorporation,
Acros Organics, and Alfa Aesar. All amine final products were converted
into either the oxalate or hydrochloride salt. Spectroscopic data
and yields refer to the free base form of compounds. Flash chromatography
was performed using silica gel (EMD Chemicals, Inc.; 230–400
mesh, 60 Å) by using a Teledyne ISCO CombiFlash RF system. ¹H NMR spectra were acquired using a Varian Mercury Plus 400
spectrometer at 400 MHz. Chemical shifts are reported in parts-per-million
and referenced according to deuterated solvent for ¹H spectra
(CDCl₃, 7.26, CD₃OD, 3.31 or D₂O,
4.79). Combustion analysis was performed by Atlantic Microlab, Inc.,
(Norcross, GA), and the results agree within ±0.4% of calculated
values (Table S5). Melting point determination
was conducted using a Stanford Research Systems OptiMelt automated
melting point apparatus and are uncorrected. On the basis of NMR and
combustion data, all final compounds are >95% pure. All compounds
within this series are covered under an existing patent,⁴⁹ but only 1,^{21 (link),22 (link)}6,^{22 (link)} and 10(16 (link),21 (link)) have been previously described in the peer-reviewed
literature.

All manipulations were performed under
an inert atmosphere using a standard glove box and Schlenk techniques.
Methylene chloride, acetonitrile, chlorobenzene, and CD₂Cl₂ were stirred over CaH₂ and transferred
to the reservoir under vacuum. Toluene, hexane, THF, and C₆D₆ were distilled from benzophenone ketyl. Methylcyclohexane
(anhydrous grade), toluene, and cyclohexene used for the oligomerization
reactions were purchased from Aldrich and purified over a Na/K alloy.
Ethylene was purified by contact with molecular sieves and copper
for more than 12 h under 40 bar pressure. The ¹H NMR (400
MHz), ¹³C NMR (100 MHz), and ³¹P NMR (162 MHz)
spectra were recorded on a Varian Mercury plus 400 spectrometer. Elemental
analyses were carried out at the Analytical Center, Ajou University.
GC-flame ionization detection (GC-FID) analysis was performed on an
YL instrument 6500GC system equipped with a HP-PONA (50 m × 0.200
mm × 0.50 μm) column. CrCl₃(THF)₃,^{58 (link)} [Ag(CH₃CN)₄]⁺[B(C₆F₅)₄]⁻,^{51 (link)} [H(OEt₂)₂]⁺[B(C₆F₅)₄]⁻,^{59 (link)} and 18-aminopentatriacontane ([CH₃(CH₂)₁₆]₂CH–NH₂)^{54 ,55 (link)} were prepared by literature methods. Modified
MMAO-3A was sourced from Akzo Nobel (7.0 Al wt % in heptane).