Cyclopalladated complexes derived from diphenylhydrazones and their transmetallation reaction

Article abstract of DOI:10.1002/1521-3749(200209)628:9/10<2104::AID-ZAAC2104>3.0.CO;2-A

Mononuclear cyclopalladated complexes of type PdCl(Ph₂N-N=CR₁-C-R₂=N-NPh₂), where R₁=R2=H (2a), R₁=R₂=CH₃ (2b), and R₁=H, R₂=CH₃ (2c)

Full text of DOI:10.1002/1521-3749(200209)628:9/10<2104::AID-ZAAC2104>3.0.CO;2-A

Cyclopalladated Complexes Derived from Diphenylhydrazones and their
Transmetallation Reaction
´
´
´
Fernando Ortega-Jimenez, Elizabeth Gomez, Pankaj Sharma, M. Carmen Ortega-Alfaro, Ruben A. Toscano,
and Cecilio Alvarez-Toledano*
´
´
´
Mexico D.F. / Mexico, Instituto de Quımica-Universidad Nacional Autonoma de Mexico
Received April 15th, 2002.
Abstract. Mononuclear cyclopalladated complexes of type
PdCl(Ph2N-NϭCR1-C-R2ϭN-NPh2), where R1ϭR2ϭH (2a), R1ϭ
R2ϭCH3 (2b), and R1ϭH, R2ϭCH3 (2c) were synthesized by the
reaction of palladium chloride and hydrazones. Additionally,
the reaction of the complex 2c towards lithium phenylacetylide
was studied, giving Ph2NϪNϭC(CH3)ϪCHϭNϪN(Ph)(o-C6H4-
ϪCϵCϪPh) (3) . The complexes 2a-2c and compound 3 were
characterized by IR, Mass, 1H, 13C, and 2D NMR spectroscopy.
X-ray structure of complex 2c was also determined.
Keywords: Palladium; Cyclopalladated complexes; Hydrazones;
Transmetallation; Crystal structure
Cyclopalladierte Komplexe durch Transmetallierungsreaktion mit Diphenylhydrazonen
Inhaltsübersicht. Einkernige Palladiumkomplexe der Art
PdCl(Ph2N-NϭCR1-C-R2ϭN-NPh2), mit R1ϭR2ϭH (2a), R1ϭ
R2ϭCH3 (2b) und R1ϭH, R2ϭCH3 (2c) wurden durch Reaktion
von Palladiumchlorid mit Hydrazonen dargestellt. Zusätzlich
wurde die Reaktion des Komplexes 2c mit Lithiumphenylacetylid
untersucht, die Ph2NϪNϭC(CH3)ϪCHϭNϪN(Ph)(o-C6H4-
ϪCϵCϪPh) (3) ergab. Die Komplexe 2a-c und die Verbindung 3
1
wurden durch IR-, Massen-, H-, 13C- und 2D-Spektroskopie cha-
rakterisiert. Eine Röntgenstrukturanalyse von 2c wurde ebenfalls
vorgenommen.
Introduction
Results and Discussion
The ligands 1aϪ1c were prepared by condensation reaction
of N,N-diphenyl hydrazine with the corresponding 1,2-di-
carbonylic compounds. The reaction of 1aϪ1c with PdCl2
afforded cyclopalladated complexes 2aϪ2c (Scheme 1).
The IR spectra of ligands 1aϪ1c show an absorption
band at 1590cmϪ1 corresponding to ν(CϭN) vibration.
This band shows a slight shift (ϳ2Ϫ5 cmϪ1) to higher fre-
quency after cyclopalladation. The FABϩ mass spectra
show molecular ions m/z ϭ 530 and m/z ϭ 544 for 2a and
2c respectively. A molecular ion peak could not be observed
for compound 2b, but ion peak observed at m/z ϭ 523 re-
presents the molecular ion with loss of a chlorine atom.
The 1H and 13C data are reported in Table 1. The assign-
ments of the parameters are based on 2D experiments.
Palladium complexes have been the subject of interest due
to their applications in organic synthesis [1, 2]. Various
cyclopalladated complexes with tridentate N-donor ligands
e.g. azines, oximes [3], hydrazones [4Ϫ11] have been re-
ported affording to mononuclear structures, while triden-
tate imines present dinuclear as well as mononuclear struc-
tures [12, 13].
It has been reported earlier that cyclopalladated com-
plexes show reactivity towards alkynes, alkenes, CO and
isocyanides [1, 2, 14]. Mono-, bis- and tris-insertions of
alkynes in cyclopalladated complexes are known in litera-
ture [2, 15, 16]. Reports on insertion of alkynes into the
σ(Pd-Csp2,ferrocene) bond show different reactivity to that of
σ(Pd-Csp2,aryl) bond [17Ϫ20].
1
The H spectra of 2a؊2c show upfield shifts for the aro-
matic protons with respect to free ligands 1aϪ1c. Proton
present at ortho position to the Pd-C bond (H-3) was
strongly shielded after cyclopalladation in comparison to
protons present at meta and para positions.
We report herein, the synthesis and characterization of
some new palladium complexes derived from N,N-di-
phenylhydrazones. The transpalladation of these complexes
on reaction with lithium phenylacetylide was also studied.
1
Similar to H NMR spectra, 13C NMR data of 2a؊2c
reveal that the aromatic carbon atoms for the cyclopallad-
ated ring are shifted to higher frequencies in comparison to
the free ligand.
The molecular structure of 2c was established by single-
crystal X-ray diffraction analysis. Structural data, selected
bond lengths and angles are given in Table 2 and 3, respec-
tively. The structure of 2c shows that the palladium atom is
linked to four atoms and the bond angles at the palladium
* Dr. C. Alvarez-Toledano
Instituto de Quımica-UNAM
circuito exterior S/N, Ciudad Universitaria
´
´
Coyoacan C.P. 04510
´
´
Mexico D.F. / Mexico
e-mail address: cecilio@servidor.unam.mx, Fax; ϩ52 56162217
2104
 WILEY-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002 0044Ϫ2313/02/628/2104Ϫ2108 $ 20.00ϩ.50/0 Z. Anorg. Allg. Chem. 2002, 628, 2104Ϫ2108

Cyclopalladated Complexes
Table 1 1H and 13C NMR data for 2aϪ2c
CH3
H-3
H-4
H-5
H-6
H-oЈ
H-mЈ
H-pЈ
H-o
H-m
H-p
HCϭN
2a
5.79(1H,
dd,Jϭ7.2) Jϭ 7.1)
6.63(1H, t,6.77(1H, t,7.56 (1H, 7.16-
7.16-
7.16-
7.16-
7.16-
7.16-
7.16-
Jϭ7.1 )
dd,Jϭ7.7, 7.63(17H, 7.63(17H, 7.63(17H, 7.63(17H, 7.63(17H, 7.63(17H, 7.63(17H, m)
1.7)
6.75(1H,
m)
7.46(1H,
m)
7.48-
m)
7.40(6H,
m)
7.48-
m)
m)
2b 1.65(3H,s) 2.01(3H,s) 6.11(1H,
6.67(1H,
7.26(4H,d, 7.40(6H,t, 7.18(2H,t,
dd,Jϭ7.7, td,Jϭ 7.7, td, Jϭ7.7, dd,Jϭ7.7, 7.52(3H,m) t, Jϭ7.7)
7.52(3H,m) Jϭ7.1)
Jϭ7.7)
Jϭ7.1)
1.7)
6.68(1H,
1.7)
6.75(1H,
1.7)
7.46(1H,
1.7)
7.60-
2c 1.90(3H,s) 5.81(2H,
7.33-
7.60-
7.24(4H,d, 7.33-
7.15(2H,t, 6.34(1H,s)
dd,Jϭ7.7, td,Jϭ 7.7, td, Jϭ7.7, dd,Jϭ7.7, 7.66(3H, m) 7.38(6H,m) 7.66(3H, m Jϭ7.1)
7.38(6H,m) Jϭ7.1)
1.7)
1.7) )
1.7)
1.7)
-CϭN C-1
C-2
C-3
C-4
C-5
C-6
C-i
C-o
C-m
C-p
C-iЈ
C-oЈ
C-mЈ
C-pЈ
2a
2b
2c
126.6
174.4
172.2
130.6
136.1
135.2
143.0
148.9
148.9
110.5
112.6
111.3
125.5
125.5
125.5
131.2
146.0
136.2
129.7
130.3
146.1
129.0
128.1
129.4
129.7
130.3
125.0
129.7
148.9
130.3
129.0
129.5
129.5
125.3
125.0
130.3
122.7
122.8
159.1
159.1
159.1
156.3
Table 2 Crystallographic Data for Complex 2c
Formula
C27H23ClN4Pd
545.34
0.40 x 0.38 x 0.08
purple
Formula Weight /g molϪ1
Crystal size (mm)
Color
Crystal system
Space group
orthorhombic
Pbca
17.748(2)
14.582(2)
18.190(2)
90
4794.8(10)
8
1.511
˚
a /A
˚
b /A
˚
c /A
αϭβϭγ /°
3
˚
V /A
Z
Dcalc. /g cm3
No. of collected reflections
No. of independent reflections
No. of observed reflections
No. of parameters
Ra)
3922
3922
3922
298
0.0765
0.1361
b)
Rw
GOF
0.991
2 2
4 1/2
a) RϭΣʈFoΗ - ΗFcʈ / ΣΗFoΗ, bRw(Fo)2 ϭ [Σw(Fo2-Fc
) / ΣwFo ]
center range from 77.2(5) to 104.8(3)° giving rise to a dis-
torted square planar structure (Figure 1). The PdϪN(5)
˚
bond length (1.96 (1) A) trans to the chlorine, is slightly
˚
shorter than PdϪN(2) 2.19(1) A distance, trans to the σ-
PdϪC bond. This lengthening can be explained in terms of
the trans influence of the σ-bonded carbon atom of the aryl
group [5, 7]. It is important to notice, that the bond angle
N(5)ϪN(6)ϪC(26) 117(1)° deviates from a previously re-
Scheme 1
Z. Anorg. Allg. Chem. 2002, 628, 2104Ϫ2108
2105

´
´
F. Ortega-Jimenez, E. Gomez, P. Sharma, M. C. Ortega-Alfaro, R. A. Toscano, C. Alvarez-Toledano
˚
Table 3 Selected bond Lengths /A and Angles /° of 2c
PdϪC(27)
PdϪN(2)
PdϪN(5)
1.95(2)
2.19(1)
1.96(1)
2.29(4)
1.44(1)
1.29(2)
1.45(2)
1.38(2)
1.43(2)
1.39(2)
1.42(2)
1.34(2)
1.44(2)
C(27)ϪPdϪN(5)
N(5)ϪPdϪN(2)
N(5)ϪPdϪCl
81.8(6)
77.2(5)
177.7(4)
114.3(10)
111.8(9)
116.7(13)
117.5(13)
124.7(13)
116.7(10)
115.1 (14)
117.3(12)
132.7(13)
158.9(5)
96.3(5)
PdϪCl
C(7)ϪN(1)ϪN(2)
C(3)ϪN(2)ϪPd
N(2)ϪC(3)ϪC(4)
C(4)ϪC(3)ϪC(19)
C(4)ϪN(5)ϪN(6)
N(6)ϪN(5)ϪPd
C(26)ϪC(27)ϪPd
N(6)ϪC(26)ϪC(27)
C(28)ϪC(27)ϪPd
C(27)ϪPdϪN(2)
C(27)ϪPdϪCl
N(1)ϪN(2)
N(2)ϪC(3)
C(3)ϪC(19)
N(5)ϪN(6)
N(6)ϪC(20)
N(6)ϪC(26)
C(26)ϪC(27)
C(4)ϪN(5)
C(3)ϪC(4)
N(2)ϪPdϪCl
104.8(3)
115.1(11)
133.0(9)
125.8(13)
115.7(13)
118.6(10)
C(3)ϪN(2)ϪN(1)
N(1)ϪN(2)ϪPd
N(2)ϪC(3)ϪC(19)
N(5)ϪC(4)ϪC(3)
C(4)ϪN(5)ϪPd
Scheme 2
Conclusions
Some new cyclopalladated complexes were synthesised con-
taining N-donor imine ligands. The X-ray structure of 2c
reveals the distorted square planar coordination around the
palladium atom. Complex 2c was depalladated after the in-
sertion of PhCϵCϪ nucleophile. Other similar reactions
and their application in organic synthesis are still in pro-
gress.
Experimental Section
All reagents were obtained from commercial suppliers and used as
received. Starting hydrazones were prepared by the corresponding
ketones and N,N-diphenylhydrazine in ethanol according to re-
ported procedures [20]. Infrared spectra were obtained with a Nico-
let Magna 750 instrument. Melting points were measured on a
Metl-b Temp II and are uncorrected. 1H and 13C NMR spectra
were recorded on a Jeol Eclipse ϩ300, chemical shifts (ppm) are
relative to the TMS. The mass spectra were obtained on Jeol JMS-
AX505 HA; The X-Ray Crystallography study for 2c was done
Fig. 1 Molecular Structure for Complex 2c
˚
on a Siemens P4/PC diffractometer λ(Mo-Kα) ϭ 0.71073 A, graphite
monochromator, Tϭ 293 K, ω-2θ scan, range 1.5 < θ < 25°. Cor-
rections were done for Lorentz and polarization effects. The struc-
tures were solved by direct methods; all nonhydrogen atoms were
refined anisotropically by full least squares, (SHELXL-97) [21].
Absorption correction based on psi-scans was applied; hydrogen
atoms bound to carbon atoms inserted at calculated position with
isotropic temperature factor 1.2 times the Uiso of the parent car-
bon atom.
ported analogous 112° [7]. The Pd-C bond distance
˚
1.95(2) A is shorter than those found in similar square
planar palladium complexes [6,9,10,18] which could be as-
sociated with the overlapping of π electron cloud of aro-
matic ring to the d metal orbitals as suggested elsewhere [7].
Bis(N,NЈdiphenylhydrazone) of glyoxal (1a)
Furthermore the reaction of 2c in the presence of phenyl-
acetylene and BuLi, afforded an organic compound 3 as a
result of depalladation of complex 2c, as shown in Scheme
2. IR spectrum of compound 3 shows a band at 2219 cmϪ1
Compound 1a was prepared from 0.3 mL (2.6 mmol) of glyoxal
(40 % wt) and 1.14 g (5.2 mmol) of diphenylhydrazine. The prod-
uct was obtained as a white solid 60 % yield, m.p. 207 °C.
IR (CHCl3)νmax: 1590 ( CϭN), 1494 (CϭC) cmϪ1; MS (EI): m/z ϭ 390 [Mϩ,
(100)], 316(19), 270(10), 222 [Mϩ-N(C6H5)2, (10)], 168 [Mϩ-(C14H11N3),
(32)], 77(5), 45(12), 29(5), 4(8); 1H NMR (300 MHz, CDCl3): 7.08 (8H, dd,
Jϭ7.68, 1.65 Hz, H-o), 7.13(2H, s, HCϭN), 7.15 (4H, t, Jϭ7.68 Hz, H-p),
7.36 (8H, td, Jϭ7.68, 1.65 Hz, H-m) ppm; 13C NMR (75 MHz, CDCl3):122.5
(C-o), 124.7 (C-p), 129.8 (C-m), 136.4 (HCϭN), 143.4 (C-i) ppm.
1
which can be assigned to ν(CϵC). The H and 13C NMR
spectra show additional signals corresponding to the phe-
nylacetylene fragment, which is the result of transmetall-
ation and reductive elimination process [1,2].
2106
Z. Anorg. Allg. Chem. 2002, 628, 2104Ϫ2108

Cyclopalladated Complexes
6), 7.60-7.66 (3H, m, H-o, H-p) ppm; 13C NMR (75 MHz, CDCl3): 18.8
(CH3), 111.3 (C-3), 146.1 (C-o), 122.8 (C-4), 125.0 (C-p), 125.5 (C-5), 128.1
(C-pЈ), 129.5 (C-m), 130.3 (C-oЈ, C-pЈ), 136.1 (C-1), 136.2 (C-6), 148.9 (C-2),
159.1 (C-iЈ, C-i), 172.2 (CH3CϭN) ppm.
Bis-N,N-diphenylhydrazone of 2,3-Butanedione (1b)
Compound 1b was prepared from 0.21 mL (2.4 mmol) of 2,3-But-
anedione and 1.05 g (4.8 mmol) of diphenylhydrazine. The product
was obtained as a yellow solid 50 % yield, m.p.190.5 °C.
IR (CHCl3)νmax: 1590 ( CϭN), 1488 (CϭC) cmϪ1; MS (EI): m/z ϭ 418 [Mϩ,
(100)], 390 [Mϩ-C2H4 (5)], 250 [Mϩ- N(C6H5)2, (65)], 209(15), 182(10), 168
[Mϩ-(C16H16N3), (90)], 77(8), 4(9); 1H NMR (300 MHz, CDCl3):1.96 (6H,
CH3), 7.06-7.10 (12H, m, H-o, H-p), 7.31(8H, td, Jϭ7.71, 1.35, Hz, H-
m) ppm; 13C NMR (75 MHz, CDCl3):16.6 (CH3), 121.9 (C-o), 123.6 (C-p),
129.1 (C-m), 148.1 (C-i), 162.9 (CH3CϭN) ppm.
[N-phenyl-N-phenyl(2-phenylethenyl)-NЈ,NЈ-diphenyl hydrazone] of
methylglyoxal (3)
To a solution of 0.3 g (0.55 mmol) of 2c in diethylether, was added
a solution consisting of 0.6 mL (0.55 mmol) phenylacetylene in di-
ethylether and 0.3 mL of BuLi 1.6M at Ϫ78 °C. The reaction mix-
ture was allowed to warm to room temperature and after 4 h of
stirring the solvent was evaporated obtaining a black oil which was
chromatographed on alumina using Hexane/AcOEt as eluent. The
product was obtained as a yellow solid 20 % yield, m.p. 40 °C.
MS (FABϩ): m/z ϭ 504 [Mϩ,(11)], 404 (5), 336(20), 309(10), 295(4), 309(9),
279(22), 267(15), 167(65), 149(100), 184(15), 71(30), 57(62), 43(56), 29(23),
18(5); 1H RMN (300 MHz, CDCl3): 1.99 (3H, s, CH3), 6.99-7.24 (25H, m,
HCϭN, aromatic) ppm; 13C NMR (75 MHz, CDCl3): 15.6 (CH3), 85.6
(CϵC), 95.1 (CϵC), 115.4, 121.1, 122.7. 123.2, 123.9, 128.2, 128.5, 128.7,
128.4, 128.9, 129.0, 130.3, 130.4, 131.5, 134.1, 136.6 (HCϭN), 140.6 146.0,
148.1(C-i), 163.5.(CH3CϭN).
Bis(N,N-diphenylhydrazone) of methylglyoxal (1c)
Compound 1c was prepared from 0.35 mL (2.26 mmol) of meth-
ylglyoxal (40 % wt) and 1 g (4.5 mmol) of diphenylhydrazine. The
product was obtained as a yellow solid 80 % yield, m.p.186.5 °C.
IR (CHCl3)νmax: 1590 (CϭN), 1490 (CϭC aromatic); MS (EI): m/z ϭ 404
[Mϩ, (100)], 236 (Mϩ-N(C6H5)2, (12)), 221(10), 168 [Mϩ- (C15H14N3), (68)],
77(8); 1H NMR (300 MHz, CDCl3):1.99 (3H, s, CH3), 7.02-7.07 (6H, m, H-
o, H-p), 7.11-7.19 (7H, m, H-oЈ, H-pЈ, HCϭN), 7.28 (4H, td, Jϭ7.70,
1.65 Hz, H-m), 7.40(4H, td, Jϭ7.70, 1.65 Hz, H-mЈ) ppm; 13C NMR
(75 MHz, CDCl3):15.6 (CH3), 121.9 (C-o), 122.4(C-oЈ), 123.4 (C-p), 125.1
(C-pЈ), 129.1 (C-m), 130.0 (C-mЈ), 136.6 (HCϭN), 143.1 (C-i), 148.2 (C-iЈ),
163.5 (CH3CϭN) ppm.
1-Diphenylamino-10-chloro-5-phenyl-1,3,2-diazapalladolo[1,2-b]-
1,2,3-benzodiazapalladol (2a)
Supplementary material
Compound 2a was prepared from 0.15 g (0.385 mmol) of Bis(N,N-
diphenylhydrazone) of glyoxal (1a) and 0.136 g (0.77 mmol) of
PdCl2. the reaction mixture was stirred for 3 days at room tempera-
ture. The solid obtained was chromatographed on alumina using
Hexane/CH2Cl2 as eluent. The product was obtained as a purple
The crystallography data for the structural analysis have been de-
posited with the Cambridge Crystallographic Data Center, CCDC
185834 for compound 2c Copies of this information may be ob-
tained free of charge from to The director, CCDC, 12 Union Road,
Cambridge CB21EZ, UK (Fax: int.codeϩ(1223)336-033;e-mail for
inquiry: fileserv@ccdc.cam.ac.uk.
solid 95 % yield, m.p. 202 °Cdec
.
IR (CHCl3)νmax: 1593 (CϭN), 1488 (CϭC aromatic) cmϪ1; MS (FABϩ):
m/z ϭ 530 [Mϩ, (1)) 495[Mϩ-Cl, (3)], 307(35), 107(15), 77(10) 65(5); 1H
NMR (300 MHz, CDCl3):5.79(1H, dd Jϭ7.16 Hz, H-3), 6.63(1H, t, Jϭ7.14,
H-4), 6.77 (1H, t, Jϭ7.14 Hz, H-5), 7.16-7.63(18H, m, H-6, H-o, H-m, H-p,
H-oЈ, H-mЈ, H-pЈ, HCϭN) ppm; 13C NMR (75 MHz, CDCl3):110.5 (C-3),
125.3 (C-pЈ), 125.5 (C-5), 126.6 (HCϭN), 129.0 (C-m, C-mЈ), 129.7 (C-o, C-
p), 130.6 (C-1), 131.2 (C-6), 143.0 (C-2) ppm.
Acknowledgements. Financial support from DGAPA (IN216201) is
acknowledged. We are grateful to Luis Velasco Ibarra and Francisco
´
Javier Perez Flores for recording mass spectrometry.
1-Diphenylamino-10-chloro-5-phenyl-2,3-dimethyl-1,3,2-
diazapalladolo[1,2-b], 1,2,3-benzodiazapalladol (2b)
References
The title compound was prepared following the procedure de-
scribed for 2a from 0.17 g (0.4 mmol) of Bis(N,N-diphenylhydra-
zone) of 2,3-Butanedione (1b) and 0.15 g (0.8 mmol) of PdCl2. The
product was obtained as a purple solid (90 %), m.p. 256 °C.
IR (CHCl3)νmax: 1595 (CϭN), 1488(CϭC aromatic) cmϪ1; MS (FABϩ):
m/z ϭ 523 [Mϩ-Cl, (2)). 307(37), 243(5), 167(4), 107(15), 77(11), 65(4);1H
NMR (300 MHz, CDCl3):1.65 (3H, s, CH3), 2.01 (3H, s, CH3), 6.11 (1H,
dd, Jϭ7.68, 1.65 Hz, H-3), 6.67 (1H, td, Jϭ7.68, 1.65 Hz, H-4), 6.75 (1H,
td, Jϭ7.68, 1.65 Hz, H-5), 7.18 (2H, t, Jϭ7.14 Hz, H-pЈ), 7.26 (4H, d, H-oЈ),
7.40 (6H, t, Jϭ7.68 Hz, H-m, H-mЈ), 7.46 (1H, dd, Jϭ7.68, 1.65 Hz, H-6),
7.48-7.52 (3H, m, H-o, H-p) ppm; 13C NMR (75 MHz, CDCl3):18.8 (CH3),
112.6 (C-3), 148.9 (C-oЈ), 122.7 (C-4), 125.0 (C-pЈ), 125.5 (C-5), 128.1 (C-m),
129.5 (C-mЈ), 130.3 (C-o, C-p), 136.1 (C-1), 146.0 (C-6), 148.9 (C-2), 159.1
(C-i, C-iЈ), 174.4 (CH3CϭN) ppm
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1,6-diphenylamino-10-chloro-5-phenyl-2-methyl-1,3,2-
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´
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´
´
IR (CHCl3)νmax: 1592 ( CϭN), 1487 (CϭC aromatic) cmϪ1; MS (FABϩ):
m/z ϭ 544 [Mϩ,(0.5)], 509 [Mϩ-Cl, (2)], 307(35), 107(15), 77(10), 65(5); 1H
RMN (300 MHz, CDCl3): 1.90 (3H, s, CH3), 5.81 (1H, dd, Jϭ7.71, 1.65 Hz,
H-3), 6.34(1H, s, HCϭN), 6.68(1H, td, Jϭ7.71, 1.65, Hz, H-4), 6.75 (1H, td,
Jϭ7.71, 1.65 Hz, H-5), 7.15 (2H, t, Jϭ7.14 Hz, H-pЈ), 7.24 (4H, d, Jϭ
7.14 Hz, H-oЈ), 7.33-7.38 (6H, m, H-mЈ), 7.46 (1H, dd, Jϭ7.71, 1.65 Hz, H-
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2108
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