Copper-free cycloaddition of azide and alkyne in crystalline state facilitated by arene-perfluoroarene interactions

Article abstract of DOI:10.1039/b912337g

Facilitated by arene-perfluoroarene interactions, a 1,3-dipolar cycloaddition between azide and alkyne proceeded in the crystals at room temperature in the absence of a copper(i) catalyst, and the reaction was confirmed to be a highly regioselective process giving the 1,4-triazole product.

Full text of DOI:10.1039/b912337g

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Supporting Information
for
Copper-Free Cycloaddition of Azide and Alkyne in
Crystalline State Facilitated by Arene-Perfluoroarene
Interaction
Ben-Bo Ni, Chong Wang, Huixian Wu, Jian Pei,* and Yuguo Ma*
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Labs of Polymer
Chemistry & Physics and Bioorganic Chemistry & Molecular Engineering of Ministry of
Education, College of Chemistry, Peking University, Beijing 100871, China
Email: ygma@pku.edu.cn
Table of Contents
Page
1. Experimental Section
S2
2. 1H NMR, 13C NMR and 19F NMR spectra
S5
3. FT-IR and Raman Spectra
S19
S20
S21
4. X-ray Diffraction Pattern
5. Crystal Data and Structure Refinement
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1. Experimental Section
General Methods: Chemicals were purchased commercially and used without further
purification. All air and moisture sensitive reactions were performed under a nitrogen
atmosphere using standard Schlenk techniques. Tetrahydrofuran (THF) was freshly
distilled from sodium under N2 prior to use. Acetonitrile (CH3CN) was bubbled with
N2 for 30 minutes before use. N,N-Dimethylformamide (DMF) was dried over
molecular sieves. 1H, 13C, and 19F NMR spectra were recorded on Varian
Mercury-300 (300 MHz) spectrometer using acetone-d6 as solvents. Chemical shifts
are reported in parts per million (ppm) and coupling constants are reported in hertz
1
(Hz). H NMR chemical shifts were referenced versus TMS (0 ppm), 13C NMR
chemical shifts were referenced versus acetone-d6 (206.68 ppm) and 19F NMR
chemical shifts were referenced versus a CF3CO2H external standard (0 ppm). Mass
spectra were recorded on a VG ZAB-HS mass spectrometer. Elemental analysis was
performed using an Elementar VARIO EL elemental analyzer. Melting points were
measured on a METTLER TOLEDO Instrument DSC822 calorimeter. Infrared and
Raman spectra were recorded in solid phase. Infrared spectra were recorded on a
Bio-Rad FTS-65A FT-IR spectrometer. Raman spectra were recorded on a
Micro-Raman spectroscopy using a Renishaw System-1000 spectrometer with a 532
nm Yd-YAG laser, CCD detector, and 5x, 20x, 50x, and 80x objective lenses. X-ray
diffraction data were collected on a PHILIPS X’ Pert Pro diffractometer with an
o
X’celerator detector in the reflection mode at 30 C, using monochromatized Cu Kα
radiation. Single crystal X-ray diffraction data were collected with a NONIUS
KappaCCD diffractometer for imine 1, with graphite monochromator and Mo Kα
radiation [λ (MoKα) = 0.71073 Å]. Structures were solved by direct methods with
SHELXS-97 and refined against F2 with SHELXS-97.
Scheme S1. Synthesis of compounds 1-3.
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O
H
4-Ethynylbenzaldehyde was synthesized according to reference 1.[1]
F
F
F
N
F
F
(E)-N-(4-Ethynylbenzylidene)-2,3,4,5,6-pentafluorobenzenamine (1a). A solution
of 1.30 g (10.0 mmol) of 4-ethynylbenzaldehyde, 1.83 g (10.0 mmol) of
2,3,4,5,6-pentafluoroaniline and 19 mg (0.10 mmol) of p-MePhSO3H·H2O in 50 mL
of toluene was refluxed for 8 h. After cooling, the solvent was removed under reduced
pressure, and the residue was purified by flash column chromatography over silica gel
(petroleum ether/CH2Cl2, 3:1 with 1% Et3N) to afford 1a as a yellow solid (1.77g, 6.0
mmol, 60%). 1H NMR (300MHz, acetone-d6, ppm): δ 8.84 (s, 1H), 8.05 (m, 2H), 7.69
13
(m, 2H), 3.95 (s, 1H). C NMR (75 MHz, acetone-d6, ppm): δ 164.2, 135.5 (JC-F
=
250 Hz), 133.5 (JC-F = 250 Hz), 130.9, 127.9, 124.7, 122.5, 122.2, 78.1, 76.9. 19F
NMR (282 MHz, acetone-d6, ppm): δ -76.5, -85.6, -87.0. LR-MS (EI, m/z): 295 (M+).
Anal. Calcd. for C15H6F5N: C, 61.03; H, 2.05; N, 4.74. Found: C, 60.89; H, 1.74; N,
4.70. Mp: 112.2 oC (onset).
F
F
N3
N
F
F
(E)-4-Azido-N-(4-ethynylbenzylidene)-2,3,5,6-tetrafluorobenzenamine (1).
A
solution of 1.48 g (5.0 mmol) of 1a and 0.98 g (15 mmol) of NaN3 in 75 mL of DMF
was heated at 60 oC for 2 h. After cooling, 100 mL of brine was added and the mixture
was extracted with CH2Cl2. The combined organic phase was dried with Na2SO4.
After removal of solvent under reduced pressure, the residue was purified by flash
column chromatography over silica gel (petroleum ether/CH2Cl2, 3:1 with 1% Et3N)
to afford 1 as a yellow solid (1.02 g, 3.2 mmol, 64%). 1H NMR (300 MHz, acetone-d6,
13
ppm): δ 8.84 (s, 1H), 8.05 (m, 2H), 7.69 (m, 2H), 3.94 (s, 1H). C NMR (75 MHz,
acetone-d6, ppm): δ 163.6, 136.6 (JC-F = 250 Hz), 135.5 (JC-F = 250 Hz), 131.0, 127.8,
124.6, 122.4, 122.0, 111.4, 78.0, 76.9. 19F NMR (282 MHz, acetone-d6, ppm): δ -76.3,
-76.6. LR-MS (EI, m/z): 318 (M+). Anal. Calcd. for C15H6F4N4: C, 56.61; H, 1.90; N,
17.61. Found: C, 56.24; H, 2.18; N, 17.42. Compound 1 decomposes at temperature
above 80 oC before reaching its melting point.
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Polymer 2. A solid of 500 mg of 1 was kept on shelf in the absence of light for 14
days and the residue was washed by using acetone to afford an insoluble yellow solid
(500 mg, 99%).
Polymer 2’. A Schlenk-adapted tube was charged with 318 mg (1.0 mmol) of 1, 372
mg (1.0 mmol) of [Cu(CH3CN)4][PF6] and 50 mL of THF under nitrogen atmosphere.
After stirred for 36 h at room temperature, the mixture was filtrated and the residue
was washed with acetone to afford an insoluble yellow solid (95 mg, 30%).
F
F
N
NH2
O
F
N N
F
4-(1-(4-Amino-2,3,5,6-tetrafluorophenyl)-1H-1,2,3-triazol-4-yl)benzaldehyde (3).
Hydrolysis of polymer 2: A suspension of 100 mg of polymer 2, 2 mL of CF3COOH,
o
2 mL of water and 100 mL of CHCl3 was stirred under 30 C for three days. The
mixture was filtrated and yellow powder was recovered. A solution of Na2CO3 was
added to the reaction solution until pH > 7. The resulting mixture was extracted with
CH2Cl2 and the organic phase was dried with Na2SO4. After removal of solvent under
reduced pressure, the residue was purified by flash column chromatography over
silica gel (CH2Cl2, with 1% Et3N) to afford 3 as a white solid (40 mg, 0.12 mmol,
40%). No triazole 3’s 1,5-isomer was found.
Hydrolysis of polymer 2’: A suspension of 100 mg of polymer 2’, 2 mL of
o
CF3COOH, 2 mL of water and 100 mL of CHCl3 was stirred at 30 C for 1 day until
polymer 2’ was totally dissolved. A solution of Na2CO3 was added to the reaction
solution until pH > 7. The resulting mixture was extracted with CH2Cl2 and the
organic phase was dried with Na2SO4. After removal of solvent under reduced
pressure, the residue was purified by flash column chromatography over silica gel
(CH2Cl2, with 1% Et3N) to afford 3 as a white solid (91 mg, 0.27 mmol, 90%). Trace
amount of 4-ethynylbenzaldehyde in the hydrolysis product coming from the terminal
group of polymer 2’ was found. The different hydrolytic reactivity of polymer 2 and
polymer 2’ is likely a result of different molecular weight and crystallinity of 2 and 2’.
1H NMR (300 MHz, acetone-d6, ppm): δ 10.10 (s, 1H), 8.90 (s, 1H), 8.23 (m, 2H),
8.06 (m, 2H), 6.06 (s, 2H). 13C NMR (75 MHz, acetone-d6, ppm): δ 186.9, 141.6,
138.2 (JC-F = 250 Hz), 131.9, 131.4 (JC-F = 250 Hz), 131.3, 126.0, 125.6, 121.5, 120.7,
19
98.5. F NMR (282 MHz, acetone-d6, ppm): δ -74.3, -85.1. LR-MS (EI, m/z): 308
(M+-28). Anal. Calcd. for C15H8F4N4O: C, 53.58; H, 2.40; N, 16.66. Found: C, 53.40;
H, 2.56; N, 16.77. Mp: 220.2 oC (onset).
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2. 1H NMR, 13C NMR and 19F NMR spectra
Figure S1. 1H NMR spectrum of 1a in acetone-d6
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Figure S2. 13C NMR spectrum of 1a in acetone-d6
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Figure S3. Aromatic region of 13C NMR spectrum of 1a in acetone-d6
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Figure S4. 19F NMR spectrum of 1a in acetone-d6
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Figure S5. 1H NMR spectrum of 1 in acetone-d6
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Figure S6. 13C NMR spectrum of 1 in acetone-d6
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Figure S7. Aromatic region of 13C NMR spectrum of 1 in acetone-d6
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Figure S8. Aromatic region of 13C NMR spectrum of 1 in acetone-d6
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Figure S9. 19F NMR spectrum of 1 in acetone-d6
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Figure S10. 1H NMR spectrum of 3 in acetone-d6
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Figure S11. 13C NMR spectrum of 3 in acetone-d6
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Figure S12. Aromatic region of 13C NMR spectrum of 3 in acetone-d6
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Figure S13. Aromatic region of 13C NMR spectrum of 3 in acetone-d6
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Figure S14. 19F NMR spectrum of 3 in acetone-d6
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3. FT-IR and Raman Spectra
Figure S15. FT-IR spectra (top) and Raman spectra (bottom) of imine 1, polymer 2,
control polymer 2’ and triazole 3.
FT-IR spectra of 1, 2, 2’ and 3 indicate that after 1,3-dipolar cycloaddition of azide
and alkyne in crystal (2) and catalyzed by Cu(I) in solution (2’), the signal of azide
stretching mode decreased in intensity and disappeared, respectively. The residue
signal at 2133 cm-1 of polymer 2 came from the end group of resulting insoluble
polymer. In the FT-IR spectrum of 3, two bands emerged at 807 and 838 cm-1 that can
be assigned to triazole. Raman spectrum of polymer 2 showed a characteristic band at
962 cm-1, which can be assigned as in-plane ring bending band of triazole ring.[2,3]
Control polymer 2’ and hydrolysis product 3 also showed similar bands at 962 and
963 cm-1 in their Raman spectra, respectively, which reveals that 1,3-dipolar
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cycloaddition of azide and alkyne proceeded in the crystal of imine 1 and formed
polymer 2. However, the characteristic band at about 963 cm-1 in the Raman spectra
of 2, 2’ and 3 cannot provide distinction of 1,4-triazole and 1,5-triazole.
4. X-ray Diffraction Patterns
Figure S16. X-ray diffraction patterns of imine 1, polymer 2 (obtained from 1 in
crystals) and polymer 2’ (obtained from 1 in THF, catalyzed by Cu(CH3CN)4PF6).
Strong diffraction peaks of imine 1 were assigned in the figure.
XRD pattern of imine 1 shows multiple diffraction peaks in the 2θ range of 2 to
37 degree. Polymer 2 obtained from imine 1 in crystal also gave strong diffraction.
The similarity of XRD patterns of 1 and polymer 2 indicates that the crystal
parameter did not change significantly after 1,3-dipolar cycloaddition. Although
polymer 2’ gave low diffraction signal probably due to poor degree of crystallinity,
it gave four diffraction peaks consistent with those of polymer 2. The broad peak at
ca. 6o was from aluminium foil.
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5. Crystal Data and Structure Refinement
Table S1-1. Crystal data and structure refinement for imine 1.
Identification code
Empirical formula
Formula weight
Temperature
Imine 1
C15H6F4N4
318.24
113(2) K
Wavelength
0.71073 Å
Monoclinic
P21/c
Crystal system
Space group
Unit cell dimensions
a = 6.1856(12) Å
b = 7.2446(14) Å
c = 29.281(6) Å
1310.8(4) Å3
4
α = 90°
β = 92.57(3)°
γ = 90°
Volume
Z
Density (calculated)
Absorption coefficient
F(000)
1.613 Mg/m3
0.141 mm-1
640
Crystal size
0.18 x 0.12 x 0.10 mm3
Theta range for data collection
Index ranges
1.39 to 25.02°
-6 ≤ h ≤ 7, -8 ≤ k ≤ 8, -34 ≤ l ≤ 34
9472
Reflections collected
Independent reflections
Completeness to theta = 25.02°
Absorption correction
Max. and min. transmission
Refinement method
Data / restraints / parameters
Goodness-of-fit on F2
Final R indices [I>2sigma(I)]
R indices (all data)
Largest diff. peak and hole
2317 [R(int) = 0.043]
99.9 %
Semi-empirical from equivalents
0.9861 and 0.9751
Full-matrix least-squares on F2
2317 / 0 / 208
1.08
R1 = 0.0450, wR2 = 0.1170
R1 = 0.0545, wR2 = 0.1244
0.209 and -0.235 e. Å-3
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Table S1-2. Atomic coordinates (× 104) and equivalent isotropic displacement
parameters (Å2 × 104) for imine 1 at 113K. U(eq) is defined as one third of the trace of
the orthogonalized Uij tensor.
___________________________________________________________________________________
x
y
z
U(eq)
_______________________________________________________________________________
F(1)
F(2)
F(3)
0.98231(17)
1.10399(17)
0.44329(18)
0.31940(17)
0.8680(3)
0.7488(3)
0.6691(3)
0.6068(3)
0.6473(3)
0.8469(3)
0.9102(3)
0.7785(3)
0.5781(3)
0.5138(3)
0.4214(3)
0.3154
0.54116(16)
0.54625(16)
0.26584(16)
0.26381(15)
0.4072(3)
0.3713(3)
0.3429(3)
0.3880(2)
0.4026(3)
0.4710(3)
0.4738(3)
0.4048(3)
0.3372(3)
0.3378(3)
0.4316(3)
0.4745
0.4155(3)
0.4666(3)
0.5064
0.4582(3)
0.4929
0.3980(3)
0.3443(3)
0.3029
0.3530(3)
0.3168
0.3900(3)
0.3809(3)
0.3736
0.30217(4)
0.39079(4)
0.42653(3)
0.33829(3)
0.45636(5)
0.48857(6)
0.52161(6)
0.26939(5)
0.31691 (6)
0.33265(6)
0.37803(6)
0.41129(6)
0.39620(6)
0.35041(6)
0.25199(6)
0.2709
0.20273(6)
0.18518(7)
0.2049
0.13856(6)
0.1270
0.10903(6)
0.12652(6)
0.1069
0.17302(6)
0.1846
0.06010(7)
0.02020(7)
0.0114
0.0290(3)
0.0294(3)
0.0293(3)
0.0260(3)
0.0300(4)
0.0340(5)
0.0533(6)
0.0235(4)
0.0221(4)
0.0225(4)
0.0233(5)
0.0237(5)
0.0235(5)
0.0221(4)
0.0232(5)
0.028*
0.0227(4)
0.0256(5)
0.031*
0.0265(5)
0.032*
0.0242(5)
0.0252(5)
0.030*
0.0236(4)
0.028*
0.0299(5)
0.0404(6)
0.048*
F(4)
N(1)
N(2)
N(3)
N(4)
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
C(7)
H(7)
C(8)
C(9)
H(9)
C(10)
H(10)
C(11)
C(12)
H(12)
C(13)
H(13)
C(14)
C(15)
H(15
0.3721(3)
0.1676(3)
0.0632
0.1189(3)
0.0177
0.2740(3)
0.4786(3)
0.5824
0.5258(3)
0.6617
0.2293(3)
0.2031(4)
0.1824
____________________________________________________________________
Table S1-3. Bond lengths [Å] and angles [°] for imine 1 at 113K.
_____________________________________________________________________
F1—C2
F2—C3
F3—C5
F4—C6
N1—N2
N1—C4
N2—N3
N4—C7
N4—C1
C1—C2
C1—C6
C2—C3
1.350(2)
1.346(2)
1.348(2)
1.349(2)
1.250(2)
1.408(2)
1.124(2)
1.274(3)
1.407(2)
1.390(3)
1.392(3)
1.369(3)
C7—C8
C7—H7
8—C13
C8—C9
C9—C10
C9—H9
C10—C11
C10—H10
C11—C12
11—C14
C12—C13
C12—H12
1.466(3)
0.9300
1.393(3)
1.394(3)
1.386(3)
0.9300
1.390(3)
0.9300
1.399(3)
1.448(3)
1.381(3)
0.9300
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C3—C4
C4—C5
C5—C6
N2—N1—C4
1.391(3)
1.386(3)
1.382(3)
118.96(17)
169.5(2)
C13—H13
C14—C15
C15—H15
N4—C7—H7
0.9300
1.174(3)
0.9300
119.4
119.4
N3—N2—N1
C8—C7—H7
C7—N4—C1
C2—C1—C6
C2—C1—N4
C6—C1—N4
F1—C2—C3
F1—C2—C1
C3—C2—C1
F2—C3—C2
F2—C3—C4
C2—C3—C4
C5—C4—C3
C5—C4—N1
C3—C4—N1
F3—C5—C6
F3—C5—C4
C6—C5—C4
119.60(17)
115.66(17)
118.09(17)
125.93(18)
118.48(17)
118.91(16)
122.59(18)
119.20(17)
119.23(16)
121.57(18)
116.57(17)
127.68(18)
115.72(18)
118.73(17)
119.74(16)
121.52(17)
117.94(17)
119.90(16)
122.07(18)
121.18(17)
179.3(13)
139.37(19)
47.4(3)
178.11(16)
8.0(3)
0.5(3)
173.42(17)
0.2(3)
178.43(17)
179.66(17)
1.1(3)
178.05(16)
1.4(3)
3.7(3)
176.76(17)
11.8(3)
13—C8—C9
C13—C8—C7
C9—C8—C7
C10—C9—C8
C10—C9—H9
C8—C9—H9
C9—C10—C11
C9—C10—H10
119.33(17)
121.51(17)
119.15(17)
120.33(18)
119.8
119.8
120.05 (18)
120.0
11—C10—H10
120.0
C10—C11—C12
C10—C11—C14
C12—C11—C14
C13—C12—C11
C13—C12—H12
C11—C12—H12
C12—C13—C8
119.85(17)
121.43(18)
118.72(18)
119.75(18)
120.1
120.1
120.67(18)
119.7
119.7
176.8(2)
180.0
177.77(17)
177.51(17)
1.3(3)
F4—C6—C5
F4—C6—C1
C5—C6—C1
N4—C7—C8
C12—C13—H13
C8—C13—H13
C15—C14—C11
C14—C15—H15
C4—C5—C6—F4
F3—C5—C6—C1
C4—C5—C6—C1
C2—C1—C6—F4
N4—C1—C6—F4
C2—C1—C6—C5
N4—C1—C6—C5
C1—N4—C7—C8
N4—C7—C8—C13
N4—C7—C8—C9
C13—C8—C9—C10
C7—C8—C9—C10
C8—C9—C10—C11
C9—C10—C11—C12
C9—C10—C11—C14
C10—C11—C12—C13
C11—C12—C13—C8
C9—C8—C13—C12
C7—C8—C13—C12
C10—C11—C14—C15
C12—C11—C14—C15
C4—N1—N2—N3
C7—N4—C1—C2
C7—N4—C1—C6
C6—C1—C2—F1
N4—C1—C2—F1
C6—C1—C2—C3
N4—C1—C2—C3
F1—C2—C3—F2
C1—C2—C3—F2
F1—C2—C3—C4
C1—C2—C3—C4
F2—C3—C4—C5
C2—C3—C4—C5
F2—C3—C4—N1
C2—C3—C4—N1
N2—N1—C4—C5
N2—N1—C4—C3
N1—C4—C5—F3
C3—C4—C5—C6
N1—C4—C5—C6
F3—C5—C6—F4
178.07(16)
4.7(3)
1.6(3)
171.74(18)
179.05(17)
0.4(3)
179.39(18)
1.1(3)
177.97(18)
0.2(3)
0.6(3)
179.17(18)
0.6(3)
−0.3(3)
1.1(3)
177.92(18)
177(4)
170.25(19)
1.1(3)
0.3(3)
177.64(18)
1.0(3)
3(4)
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Table S1-4. Anisotropic displacement parameters (Å2 × 103) for imine 1 at 113K. The
anisotropic displacement factor exponent takes the form: -2π2[h2a*2U11 + ... +
2hka*b*U12 ]
___________________________________________________________________________________
U11
U22
U33
U23
U13
U12
_______________________________________________________________________________________________________
F(1)
F(2)
F(3)
F(4)
0.0233(6)
0.0211(6)
0.0295(7)
0.0222(6)
0.0285(10)
0.0297(10)
0.0422(13)
0.0256(9)
0.0248(11)
0.0216(10)
0.0177(10)
0.0280(11)
0.0234(11)
0.0186(10)
0.0245(11)
0.0235(11)
0.0225(11)
0.0213(11)
0.0268(11)
0.0266(11)
0.0216(10)
0.0293(12)
0.0407(14)
0.0369(7)
0.0356(7)
0.0353(7)
0.0277(7)
0.0385(11)
0.0453(12)
0.0918(19)
0.0235(9)
0.0194(10)
0.0213(11)
0.0214(11)
0.0208(11)
0.0237(11)
0.0275 (6)
0.0314 (6)
0.0236 (6)
0.0279 (6)
0.0228 (8)
0.0265 (10)
0.0258 (10)
0.0214 (8)
0.0223 (10) 0.0049(8)
0.0251 (10) 0.0041(8)
0.0305 (11) 0.0030(8)
0.0222 (9)
0.0238 (10) 0.0025(8)
0.0006(5) 0.0078(5)
0.0031(5) 0.0016(5)
0.0041(5) 0.0053(5)
0.0030(5) 0.0000(5)
0.0017(5)
0.0031(5)
0.0044(5)
0.0002(5)
N(1)
N(2)
N(3)
N(4)
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
C(7)
C(8)
C(9)
C(10)
C(11)
C(12)
C(13)
C(14)
C(15)
0.0026(8)
0.0056(9)
0.0010(7) 0.0020(7)
0.0036(8) 0.0018(8)
0.0234(12) 0.0012(9)
0.0022(11)
0.0013(6)
0.0014(8)
0.0015(7)
0.0001(7)
0.0027(8)
0.0057(8)
0.0014(8)
0.0012(8)
0.0011(8)
0.0039(8)
0.0021(8)
0.0052(8)
0.0029(8)
0.0009(8)
0.0021(8)
0.0011(8)
0.0007(8)
0.0038(8)
0.0196(10) 0.0277 (10) 0.0021(8)
0.0206(10)
0.0207(10)
0.0244(11)
0.0254(11)
0.0202(11)
0.0223(11)
0.0219(11)
0.0271(12)
0.0501(15)
0.0248 (10) 0.0007(8)
0.0240 (10)
0.0300 (10)
0.0322 (11)
0.0254 (10)
0.0269 (10)
0.0270 (10) 0.0000(8)
0.0329 (12) 0.0020(9)
0.0296 (12) 0.0100(11)
0.0033(8) 0.0011(8)
0.0006(8) 0.0034(8)
0.0007(8)
0.0002(8)
0.0031(9)
0.0023(8)
0.0048(9) 0.0016(9)
0.0013(8) 0.0006(8)
0.0011(9) 0.0031(8)
0.0013(8)
0.0016(8) 0.0025(8)
0.0036(9) 0.0007(9)
0.0074(10) 0.0033 (10)
_____________________________________________________________________
References:
[1] W. B. Austin, N. Bilow, W. J. Kelleghan, K. S. Y. Lau, J. Org. Chem. 1981, 46,
2280-2286.
[2] C. Törnkvist, J. Bergman, B. Liedberg, J. Phys. Chem. 1991, 95, 3119.
[3] A. A. Jbarah, K. Banert, R. Holze, Vib. Spectrosc. 2007, 44, 142.
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