Synthesis and polymerization of sterically hindered 2,5-diphenyl- and 2,3,5-triphenyl-1-vinylpyrroles

Article abstract of DOI:10.1007/s11172-009-0017-3

Sterically hindered 2,5-diphenyl-and 2,3,5-triphenyl-1-vinylpyrroles have been obtained by the vinylation of the corresponding NH-pyrroles with acetylene in superbasic catalytic system KOH-DMSO in up to 78% yield. 2,3,5-Triphenyl-1- vinylpyrrole has also

Full text of DOI:10.1007/s11172-009-0017-3

Russian Chemical Bulletin, International Edition, Vol. 58, No. 1, pp. 115—118, January, 2009
115
Synthesis and polymerization of sterically hindered
2,5ꢀdiphenylꢀ and 2,3,5ꢀtriphenylꢀ1ꢀvinylpyrroles*
O. V. Petrova,a M. V. Markova,a L. N. Sobenina,a L. V. Morozova,a A. I. Mikhaleva,a
S.ꢀH. Hyun,b and B. A. Trofimova
aA. E. Favorsky Irkutsk Institute of Chemistry,
Siberian Branch of the Russian Academy of Sciences,
1 ul. Favorskogo, 664033 Irkutsk, Russian Federation.
Fax: +7 (3952) 41 9346. Eꢀmail: boris_trofimov@irioch.irk.ru
bSamsung Advanced Institute of Technology, Display Device & Material Lab.
San 14ꢀ1, NongseoꢀDong, GiheungꢀGu, Yongin, GyeonggiꢀDo 446ꢀ712, Korea.
Fax: +82 31 280 9349. Eꢀmail: romeos.hyun@samsung.com
Sterically hindered 2,5ꢀdiphenylꢀ and 2,3,5ꢀtriphenylꢀ1ꢀvinylpyrroles have been obtained
by the vinylation of the corresponding NHꢀpyrroles with acetylene in superbasic catalytic
system KOH—DMSO in up to 78% yield. 2,3,5ꢀTriphenylꢀ1ꢀvinylpyrrole has also been
obtained in 75% yield by the regioselective bromination of 2,3ꢀdiphenylꢀ1ꢀvinylpyrrole with
subsequent crossꢀcoupling of 5ꢀbromoꢀ2,3ꢀdiphenylꢀ1ꢀvinylpyrrole with phenylmagnesium
bromide in the presence of dichloro[1,1´ꢀbis(diphenylphosphino)ferrocene]palladium(II).
2,5ꢀDiphenylꢀ and 2,3,5ꢀtriphenylꢀ1ꢀvinylpyrroles undergo a freeꢀradical polymerization
(AIBN, 80 °C) to form oligomers in 11 and 27% yield, respectively.
Key words: pyrroles, 2,5ꢀdiphenylꢀ1ꢀvinylpyrrole, 2,3,5ꢀtriphenylꢀ1ꢀvinylpyrrole, vinylation,
crossꢀcoupling, polymerization.
In the last decades, a growing interest to pyrroles is
cased by their wide synthetic possibilities and enormous
biological and technical potential.1—4 A variety of medicines,
including antitumor, are obtained on the basis of pyrroles.5,6
Pyrroles are also the basis for development of lightꢀemitꢀ
ting diodes, electroconducting coatings,7 they are used as
components for modern rechargeable lithium batteries.8
The presence of a vinyl group in the structure of pyrꢀ
role derivatives increases their synthetic potential, allows
one to obtain unique polymers: electroconducting mateꢀ
rials and organic metals for the processes of transformaꢀ
tion of the solar energy and recording of information,9—11
sorbents for noble metals,12 biologically active compounds
and plant protection substances,11,13 modificators of polyꢀ
mers and polymeric azo dyes.14,15
Due to the discovery and systematic development of
the reaction of ketoximes with acetylene in superbasic
media (the Trofimov reaction), a possibility to synthesize
a wide range of substituted pyrroles in one preparative
stage has been appeared.1—3
Vinylation of phenylpyrroles with acetylene proceeds
in the catalytic system KOH—DMSO at both high and
atmospheric pressure.1,16—18 In the latter case (100 °C, 5 h),
2,5ꢀdiphenylꢀ1ꢀvinylpyrrole is formed only in the trace
amounts (2—3%), whereas vinylation of 2,3ꢀdiphenylꢀ
pyrrole under the same conditions leads to 2,3ꢀdiphenylꢀ
1ꢀvinylpyrrole in 35% yield (see Ref. 18). Conducting
the reaction under pressure of acetylene (the initial presꢀ
sure of 10—12 atm) allows one to increase the yield of
2,3ꢀdiphenylꢀ1ꢀvinylpyrrole up to 72% (100 °C, 3 h).16,17
The present work deals with the synthesis of 2,5ꢀdipheꢀ
nylꢀ and 2,3,5ꢀtriphenylꢀ1ꢀvinylpyrroles and their polyꢀ
merization.
Experiments showed that, in contrast to 2,3ꢀdiphenylꢀ
pyrrole, 2,5ꢀdiphenylpyrrole (1) is vinylated under more
drastic conditions: 2,5ꢀdiphenylꢀ1ꢀvinylpyrrole (2) is not
detected (1H NMR) in the reaction medium after 3 h at
90—110 °C (the initial pressure of acetylene was 11—12 atm).
An increase in the temperature up to 140 °C (the initial
pressure of acetylene was 11—12 atm, 3 h) allowed us to
obtain vinylpyrrole 2 in 20% yield (Scheme 1). And only
on conducting the reaction at 150 °C (the initial pressure
of acetylene was 11—12 atm, 3 h), the yield of vinylpyrrole
2 reached 78%.
The low vinylation rate of 2,5ꢀdiphenylpyrrole (1),
obviously, results from the strong steric hindrance of the
anionic center on the nitrogen atom by two phenyl subꢀ
stituents.
* Dedicated to Academician A. I. Konovalov on his 75th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 115—118, January, 2009.
1066ꢀ5285/09/5801ꢀ0115 © 2009 Springer Science+Business Media, Inc.

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Petrova et al.
Scheme 1
Scheme 3
R = H (1, 2), Ph (3, 4)
R = H (2, 7), Ph (4, 8)
Conditions: KOH—DMSO, 150 °C.
and CH groups of the polymeric chain (2961, 2927,
2869 cm–1) are present. The absorption bands of benzene
and pyrrole rings remain in the IR spectra.
Under comparable conditions (150 °C, the initial presꢀ
sure of acetylene of 11—12 atm, 4 h), 2,3,5ꢀtriphenylꢀ
pyrrole (3) reacts with acetylene to form 2,3,5ꢀtriphenylꢀ
1ꢀvinylpyrrole (4) (77% yield).
As it is characteristic of polymers, all the signals are
1
broadened in the H NMR spectra. The signals for the
protons of the vinyl group (4.46—4.58, 4.70—4.80, and
6.67—6.81 ppm) disappear from them and the broad
signals for the protons of the CH and CH2 groups of the
polymeric chain appear in the regions 3.73—4.27 and
2.13—3.17 ppm. The protons of the benzene rings
resonate as a wide signal with the maximum at 7.25 ppm
for 7 and 7.09 ppm for 8, the signals for the protons of the
pyrrole ring are observed at 6.05 and 6.50 ppm for comꢀ
pounds 7 and 8, respectively.
2,3,5ꢀTriphenylꢀ1ꢀvinylpyrrole (4) was also obtained
by the bromination of 2,3ꢀdiphenylꢀ1ꢀvinylpyrrole (5)
with Nꢀbromosuccinimide19 with subsequent Pdꢀcatalyzed
crossꢀcoupling20 of thus obtained 5ꢀbromoꢀ2,3ꢀdiphenylꢀ
1ꢀvinylpyrrole (6) with phenylmagnesium bromide
(Scheme 2).
Scheme 2
2,5ꢀDiphenylꢀ (2) and 2,3,5ꢀtriphenylꢀ1ꢀvinylpyrroles
(4) under study are characterized by low activity in the
radical polymerization. Thus, the yield of poly(2,5ꢀdipheꢀ
nylꢀ1ꢀvinylpyrrole) (7) on polymerization in benzene (the
ratio monomer : benzene was 2 : 1, 80 °C, 160 h) is only
2%. In the absence of benzene (polymerization in the neat
mass), the yield of polymer 7 did not exceed 6%. The use
of special method, viz., the addition of an initiator into the
melted monomer, allowed us to raise the yield up to 11%.
Poly(2,3,5ꢀtriphenylꢀ1ꢀvinylpyrrole) (8) was obtained
under similar conditions in 27% yield for 115 h (Fig. 1).
The reduced activity of 2,5ꢀdiphenylꢀ1ꢀvinylpyrrole
in the polymerization, obviously, is caused by the limited
Reagents and conditions: i. Nꢀbromosuccinimide (NBS), THF,
8—12 °C; ii. dichloro[1,1´ꢀbis(diphenylphosphino)ferrocene]ꢀ
palladium(II) (PdCl2•dppf) (1 mol.%), THF, 60—63 °C.
Y (%)
8
25
20
It was found that 1ꢀvinylphenylpyrroles 2 and 4 can
polymerize in the presence of 2,2´ꢀazoꢀbis(isobutyroꢀ
nitrile) (AIBN) with the formation of oligomers 7 and 8
(molecular mass 1400 and 1500, respectively, Scheme 3),
well soluble in organic solvents (benzene, acetone, chloꢀ
roform).
According to the IR and 1H NMR spectroscopic data,
the oligomers synthesized have the structure shown in
Scheme 3.
15
7
10
5
0
70
90
110
115
140 t/h
In the IR spectra of polymers 7 and 8, the absorption
bands of the vinyl group (1640, 849, 577 cm–1)1,21 are
absent and the bands of stretching vibrations of the CH2
Fig. 1. Yields (Y) of poly(2,5ꢀdiphenylꢀ1ꢀvinylpyrrole) (7) and
poly(2,3,5ꢀtriphenylꢀ1ꢀvinylpyrrole) (8) versus polymerization
time.

NꢀVinylpolyphenylpyrroles
Russ.Chem.Bull., Int.Ed., Vol. 58, No. 1, January, 2009
117
838, 781, 765, 754, 729, 697, 653, 577. 1H NMR, δ: 7.42 (m,
4 H, Ph); 7.36 (m, 4 H, Ph); 7.28 (m, 2 H, Ph); 6.81 (dd, 1 H,
Hx, JH ,H = 8.8 Hz, JH ,H = 15.9 Hz); 6.31 (s, 2 H, H(3),
accessibility of the monomer to the growing radical
shielded by the phenyl groups.
The more than twoꢀfold increase in the yield of polymer
8 in comparison with polymer 7, apparently, is caused by
the positive steric effect, namely, by the increase in the
rotation angle of the phenyl substituent at position 2 with
respect to the pyrrole ring due to the steric interaction
with the phenyl substituent at position 3. This should lead
to the steric deshielding of the Nꢀvinyl group.
The formation of oligomers characteristic of 1ꢀvinylꢀ
phenylpyrroles 2 and 4 under study, as in the case of other
1ꢀvinylpyrroles, probably, should be referred to the proꢀ
cesses of the chain transfer on a monomer.1,22
In conclusion, we found conditions for the vinylation
of sterically hindered 2,5ꢀdiphenylꢀ and 2,3,5ꢀtriphenylꢀ
pyrroles with acetylene. Alternatively 2,3,5ꢀtriphenylꢀ
1ꢀvinylpyrrole was prepared by bromination of 2,3ꢀdipheꢀ
nylꢀ1ꢀvinylpyrrole with subsequent crossꢀcoupling of
5ꢀbromoꢀ2,3ꢀdiphenylꢀ1ꢀvinylpyrrole with phenylmagꢀ
nesium bromide. The possibility to obtain oligomers of
2,5ꢀdiphenylꢀ and 2,3,5ꢀtriphenylꢀ1ꢀvinylpyrroles under
conditions of radical polymerization was demonstrated.
x
x
H(4)); a4.81 (d, 1 H, H ,bJH ,H = 8.8 Hz); 4.58 (d, 1 H, Hb,
a
x
JH ,H = 15.9 Hz). 13C NMR,aδ: 135.4, 133.6, 131.5, 129.4, 128.2,
b
127.0x, 110.9, 109.5.
2,3,5ꢀTriphenylꢀ1ꢀvinylpyrrole (4). A. 2,3,5ꢀTriphenylpyrrole
(3) (2.1 g, 7.1 mmol), KOH (0.63 g, 30 wt%, 11.2 mmol), and
DMSO (50 mL) were placed in a 0.25 L rotary steel autoclave,
acetylene was passed through until saturation, and the mixture
was heated for 4 h at 150 °C. After cooling, the reaction mixture
was extracted with hexane (5×50 mL), the extracts were washed
with water (2×70 mL), and dried with MgSO4. After the solvent
was evaporated, the product was isolated by column chromatoꢀ
graphy (Al2O3, hexane) to obtain 2,3,5ꢀtriphenylꢀ1ꢀvinylpyrrole
(4) (1.76 g, 77%), white crystals, m.p. 76—78 °C. Found (%):
C, 89.86; H, 5.89; N, 4.20. C24H19N. Calculated (%): C, 89.68;
H, 5.96; N, 4.36. IR, ν/cm–1: 3057, 3030, 1950, 1888, 1813,
1640, 1603, 1503, 1485, 1468, 1406, 1388, 1358, 1298, 1115,
1072, 963, 913, 762, 696. 1H NMR, δ: 7.49 (m, 2 H, Ph);
7.38—7.30 (m, 7 H, Ph); 7.17 (m, 5 H, Ph); 7.09 (m, 1 H, Ph);
6.67 (dd, 1 H, Hx, JH ,H = 8.8 Hz, JH ,H = 15.8 Hz); 6.50 (s,
x
1 H, H(4)); 4.70 (d, 1 aH,xH , JH ,H = 8b.8 Hz); 4.46 (d, 1 H, Hb,
a
a
x
JH ,H = 15.8 Hz). 13C NMR, δ: 136.6, 135.1, 134.1, 133.7,
b
132.5x,132.1, 130.1, 129.2, 129.1, 128.9, 128.5, 127.9, 126.4,
124.9, 112.1, 109.7.
Experimental
B. Dichloro[1,1´ꢀbis(diphenylphosphino)ferrocene]pallaꢀ
dium(II) (0.042 g, 1 mol.%, 5.7•10–5 mmol) and a solution of
PhMgBr in THF (1 M, 13.2 mL) were sequentially added to a
solution of 5ꢀbromoꢀ2,3ꢀdiphenylꢀ1ꢀvinylpyrrole (6) (1.85 g,
5.7 mmol) in THF (5 mL) under argon and the mixture was
heated for 3 h (60—63 °C). After cooling, the reaction mixture
was diluted with water (60 mL), extracted with ether (3×20 mL),
and dried with Na2SO4. After the solvent was evaporated, the
product was isolated by column chromatography (Al2O3, hexane)
to obtain 2,3,5ꢀtriphenylꢀ1ꢀvinylpyrrole (4) (1.37 g, 75%).
5ꢀBromoꢀ2,3ꢀdiphenylꢀ1ꢀvinylpyrrole (6). NꢀBromosucꢀ
cinimide (NBS) (1.07 g, 6.0 mmol) was added to a solution
of 2,3ꢀdiphenylꢀ1ꢀvinylpyrrole (5) (1.23 g, 5.0 mmol) in THF
(20 mL) cooled to 10—12 °C, the mixture was stirred until
complete dissolution (10—15 min) and kept in refrigerator
(8—10 °C) for 18 h. After that, sodium sulfate (1.0 g) was added
to the mixture, the solvent was evaporated under reduced
pressure, the residue was diluted with CCl4 (5 mL), a precipitate
was filtered off and washed with CCl4 (3 mL). After evaporation
of the solvent, the residue was passed through a layer of Al2O3
(light petroleum) to obtain 5ꢀbromoꢀ2,3ꢀdiphenylꢀ1ꢀvinylpyrrole
(6) (1.06 g, 65%), beige crystals, m.p. 70—71 °C. Found (%):
C, 66.46; H, 4.25; Br, 23.98; N, 4.38. C18H14BrN. Calculated (%):
C, 66.68; H, 4.35; Br, 24.65; N, 4.32. IR, ν/cm–1: 3081, 3048,
2923, 2851, 1957, 1888, 1636, 1600, 1489, 1459, 1447, 1406,
1351, 1319, 1294, 1179, 1069, 1029, 958, 916, 896, 786, 761,
739, 697, 576. 1H NMR, δ: 7.40 (m, 3 H, Ph); 7.24 (m, 2 H,
Ph); 7.15 (m, 2 H, Ph); 7.10 (m, 3 H, Ph); 6.62 (dd, 1 H, Hx,
JH ,H = 9.0 Hz, JH ,Hx = 15.6 Hz); 6.51 (s, 1 H, H(4)); 4.98 (d,
IR spectra of compounds synthesized in the region
400—4000 cm–1 were recorded in KBr pellets on a Bruker IFSꢀ25
spectrometer. NMR spectra were recorded on a Bruker DPX 400
spectrometer (400.13 (1H) MHz, 100.6 MHz (13C)); CDCl3 was
the solvent, HMDS was the internal standard. 2,3ꢀDiphenylꢀ
1ꢀvinylpyrrole (5) was synthesized according to the procedure
described earlier,17 the catalyst PdCl2•dppf was obtained
according to the known procedure.23
Polymerization of 2,5ꢀdiphenylꢀ1ꢀvinylpyrrole and 2,3,5ꢀtriꢀ
phenylꢀ1ꢀvinylpyrrole was carried out under argon in the
presence of 2,2´ꢀazoꢀbis(isobutyronitrile) (AIBN), which was
recrystallized twice from methanol. Solvents (benzene, hexane)
were purified by known procedures.24
Molecular mass of poly(2,5ꢀdiphenylꢀ1ꢀvinylpyrrole) (7) was
determined on a Waters gel chromatograph with the channel
refractometric detector at 25 °C with THF being the eluent.
Molecular mass of poly(2,3,5ꢀtriphenylꢀ1ꢀvinylpyrrole) (8) was
determined by the isopiestic method in benzene at 60 °C with
azobenzene being the standard.25
2,5ꢀDiphenylꢀ1ꢀvinylpyrrole (2). 2,5ꢀDiphenylpyrrole (1)
(2.0 g, 9.1 mmol), KOH (0.60 g, 30 wt%, 10.7 mmol), and
DMSO (50 mL) were placed in a 0.25 L rotary steel autoclave,
acetylene was passed through until saturation, and the mixture
was heated for 3 h at 150 °C. After cooling, the reaction mixture
was diluted with water (250 mL) and extracted with hexane
(5×50 mL). The extracts were washed with water (2×70 mL),
and dried with K2CO3. After the solvent was evaporated, the
residue was distilled in vacuo (7•10–2 Torr, 142—162 °C) to
obtain 2,5ꢀdiphenylꢀ1ꢀvinylpyrrole (2) (1.74 g, 78%), beige
crystals, m.p. 80—81 °C. Found (%): C, 88.20; H, 6.08; N, 5.69.
C18H15N. Calculated (%): C, 88.13; H, 6.16; N, 5.71. IR,
ν/cm–1: 3049, 1947, 1882, 1813, 1641, 1600, 1548, 1486, 1448,
1407, 1388, 1324, 1297, 1239, 1122, 1075, 968, 915, 896, 849,
a
x
1 H, Ha, JH ,H = 9b.0 Hz); 4.96 (d, 1 H, Hb, JH ,Hx = 15.6 Hz).
b
x
13C NMR, aδ: 135.9, 133.1, 132.2, 132.0, 131.6, 129.3, 129.0,
128.9, 128.8, 126.8, 113.8, 111.4.
Polymerization (general procedure). 2,2´ꢀAzoꢀbis(isobutyroꢀ
nitrile) (5 wt%) was added to the melted monomer 2 or 4 with
stirring and the mixture was incubated at 80 °C. The polymers 7

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Petrova et al.
and 8 obtained were purified by reprecipitation from benzene
with hexane and dried in vacuo until the weight is constant.
Poly(2,5ꢀdiphenylꢀ1ꢀvinylpyrrole) (7). Polymer 7 (0.28 g,
11%) was obtained from 2,5ꢀdiphenylꢀ1ꢀvinylpyrrole (2) (2.54 g,
10.4 mmol) in the presence of AIBN (0.127 g, 0.77 mmol) after
140 h, white powder, m.p. 136—142 °C, molecular mass 1400.
Found (%): C, 88.63; H, 5.96; N, 5.38. C18H15N. Calculated
(%): C, 88.13; H, 6.16, N, 5.71. IR, ν/cm–1: 3056, 3026, 2964,
2927, 2864, 1602, 1575, 1485, 1465, 1445, 1374, 1313, 1222,
1202, 1176, 1156, 1071, 1027, 968, 915, 757, 701, 667. 1H NMR,
δ: 7.26—7.11 (Ph); 6.01 (H(3), H(4)); 4.27 (N—CH); 2.12 (CH2).
Poly(2,3,5ꢀtriphenylꢀ1ꢀvinylpyrrole) (8). Polymer 8 (0.66 g,
27%) was obtained from 2,3,5ꢀtriphenylꢀ1ꢀvinylpyrrole (4) (2.44 g,
7.6 mmol) in the presence of AIBN (0.122 g, 0.75 mmol) after
115 h, beige powder, m.p. 244—254 °C, molecular mass 1500.
Found (%): C, 89.78; H, 5.90; N, 4.30. C24H19N. Calculated
(%): C, 89.68; H, 5.96; N, 4.36. IR, ν/cm–1: 3054, 2964, 2926,
2867, 1601, 1501, 1485, 1466, 1447, 1406, 1389, 1298, 1277,
1115, 1072, 913, 760, 696. 1H NMR, δ: 7.49—7.09 (Ph); 6.50
(H(4)); 3.73 (N—CH); 3.17 (CH2).
13. L. V. Morozova, A. I. Mikhaleva, M. V. Markova, O. Yu.
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Received March 12, 2008;
in revised form November 6, 2008