BULLETIN OF THE
Article
Effects of Substituents on NMR and Mass Spectra
KOREAN CHEMICAL SOCIETY
H
H
H
OC
H
3
H
OC
H
OC
+
3
3
+
H
H
H
H
-
:
2C
2C
m z
/
122 100
%
)
(
Scheme 4. McLafferty cleavage observed in 2e.
4. For example,H. S. H. Lee, H. J. Jeon, J. S. Yu, C. K. Lee,
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Experimental
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7, 420.
NMR spectra were recorded on a Bruker DPX-400 FT
NMR spectrometer (Rheinstetten, Germany) in the Central
Lab of Kangwon National University at 400 MHz for H
1
and 100 MHz for 13C and were referenced to tetramethylsi-
lane. Mass spectra were obtained using a JEOL JMS-700
mass spectrometer (Akishima, Japan) at 20 eV. The solu-
tion for the NMR spectrum was prepared by dissolving the
appropriate amount of 2 in a 1-mL volumetric flask to
make the concentration 0.1 M in chloroform-d. A portion
(0.6 mL) of the solution was transferred inꢀto a 5-mm NMR
tube, and the spectrum was obtained at 20 C.
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Preparations of m- or p-substituted chalcones (1) were
carried out from the commercially available benzaldehydes
and acetophenones by following the procedures in the
literature.23
Reduction of m- and p-substituted chalcones (1) to 1,3-
diarylpropanes (2). An illustrative procedure for the conver-
sion of 1d to 2d is as follows: A mixture of 1d (110 mg,
0.53 mmoles), Et3SiH (0.70 mL, 4.38 mmoles), and
CF3CO2H (0.65 mL, 8.53 mmoles) in a sealed tube was
ꢀ
stirred at 80 C for 5 h. The resulting liquid was poured
into dichloromethane (50 mL) and washed with 1M NaOH
(3 × 20 mL) and water (10 mL), successively. The organic
layer was dried over MgSO4 and then evaporated, yielding
a viscous liquid, which was chromatographed (silica gel,
EtOAc:hexane = 1:9) to obtain the pure product 2d in 70%
yield.
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& Sons, New York, NY,
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Acknowledgments. We thank Dr. Gary Kwong for help in
preparing the manuscript. This research was supported by
2015 Research Grant from the Kangwon National Univer-
sity (No. 520150200).
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Bull. Korean Chem. Soc. 2016, Vol. 37, 538–543
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