Photochemical reactions of acyl iodides with aryl halides

Article abstract of DOI:10.1134/S1070428013010041

Photochemical reactions of acyl iodides RC(O)I (R = Me, Ph) with aryl halides, fluoro-, chloro-, and bromobenzenes, 1,4-dibromobenzene, 2- and 3-bromotoluenes, and 4-bromo-1,2-dimethylbenzene, were studied. Acetyl iodide reacted with chloro- and bromobenzenes and 1,4-dibromobenzene according to the exchange pattern to give iodobenzene and 1,4-diiodobenzene, respectively. No halogen exchange was observed in the reactions of acetyl iodide with fluorobenzene and hexafluorobenzene. Benzoyl iodide failed to react with chloro- and brombenzene under UV irradiation but underwent polycondensation with formation of black nonfusible oligomers which were found to possess paramagnetic and semiconducting properties. Ultraviolet irradiation of a mixture of MeCOI with 2- or 3-bromotoluene, as well as with 4-bromo-1,2-dimethylbenzene, also led to the formation of polymeric products as a result of polycondensation of aryl iodides formed initially via replacement of bromine by iodine. Irradiation of benzoyl iodide in 2- or 3-bromotoluene involved recombination of benzoyl radicals to give benzil as the only product.

Full text of DOI:10.1134/S1070428013010041

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2013, Vol. 49, No. 1, pp. 17–21. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © M.G. Voronkov, N.N. Vlasova, L.I. Belousova, A.V. Vlasov, T.I. Vakul’skaya, G.F. Prozorova, S.S. Khutsishvili, 2013, published in
Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 1, pp. 27–31.
Dedicated to Full Member of the Russian Academy of Sciences
G.A. Tolstikov on his 80th anniversary
Photochemical Reactions of Acyl Iodides with Aryl Halides
M. G. Voronkov, N. N. Vlasova, L. I. Belousova, A. V. Vlasov, T. I. Vakul’skaya,
G. F. Prozorova, and S. S. Khutsishvili
Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
e-mail: andreivl@irioch.irk.ru
Received June 6, 2012
Abstract—Photochemical reactions of acyl iodides RC(O)I (R = Me, Ph) with aryl halides, fluoro-, chloro-, and
bromobenzenes, 1,4-dibromobenzene, 2- and 3-bromotoluenes, and 4-bromo-1,2-dimethylbenzene, were
studied. Acetyl iodide reacted with chloro- and bromobenzenes and 1,4-dibromobenzene according to the
exchange pattern to give iodobenzene and 1,4-diiodobenzene, respectively. No halogen exchange was observed
in the reactions of acetyl iodide with fluorobenzene and hexafluorobenzene. Benzoyl iodide failed to react with
chloro- and brombenzene under UV irradiation but underwent polycondensation with formation of black
nonfusible oligomers which were found to possess paramagnetic and semiconducting properties. Ultraviolet
irradiation of a mixture of MeCOI with 2- or 3-bromotoluene, as well as with 4-bromo-1,2-dimethylbenzene,
also led to the formation of polymeric products as a result of polycondensation of aryl iodides formed initially
via replacement of bromine by iodine. Irradiation of benzoyl iodide in 2- or 3-bromotoluene involved
recombination of benzoyl radicals to give benzil as the only product.
DOI: 10.1134/S1070428013010041
We previously found that irradiation of acyl iodides
in arenes induces photochemical Friedel–Crafts reac-
tion [1]. For example, o- and m-xylenes with enhanced
polarity of the aromatic ring are smoothly acylated
with acetyl iodide under photochemical conditions.
Acylation of the aromatic ring was the only reaction
path in the photolysis of trimethylacetyl and valeryl
iodides in toluene. We anticipated analogous process to
occur under UV irradiation of mixtures of acyl iodides
RC(O)I (R = Me, Ph) with aryl halides, fluoro-,
chloro-, and bromobenzenes, 1,4-dibromobenzene,
2- and 3-bromotoluenes, and 4-bromo-1,2-dimethyl-
benzene.
its elemental composition corresponded to the formula
~C78H53I (C/H ratio 1.5).
Scheme 1.
O
O
hν
+
PhX
Me
I
Me
X
O
Me
+
+
PhI
+ oligomer
Me
O
X = Cl, Br.
Likewise, photochemical reaction of acetyl iodide
with an equimolar amount of bromobenzene in 50 h
gave acetyl bromide, iodobenzene (9%), and biacetyl
(16%). In this case, oligomeric product 2 with the
composition C16H13I was also isolated. Oligomers 1
and 2 are products of photochemical polyphenylation
of PhI formed in the first step; they were assigned the
formulas H(C6H4)13I and H(C6H4)3I, respectively.
However, the photolysis of acetyl iodide in chloro-
benzene gave no expected acylation product, 4-chloro-
acetophenone MeCOC6H4Cl-4. After UV irradiation of
an equimolar mixture of acetyl iodide and chloroben-
zene over a period of 29 h, we isolated acetyl chloride,
biacetyl, and iodobenzene (Scheme 1). In addition,
a black powder-like nonfusible oligomer 1 with
a layered structure was isolated. Oligomer 1 was
insoluble in water and common organic solvents, and
The reactions of acetyl iodide with chloro- and
bromobenzene are photoinduced aromatic radical sub-
17

VORONKOV et al.
18
stitution processes. The source of primary radicals is
MeCOI, as follows from the presence in the reaction
mixture of biacetyl which is the product of combina-
tion of acetyl radicals.
1686 cm–1, respectively, indicated the presence in their
molecules of a carbonyl group conjugated with a ben-
zene ring. Presumably, oligomers 3 and 4 are products
of photochemical polycondensation of benzoyl iodide
via its autoacylation accompanied by photochemical
iodination of the aromatic ring. Their structure may
be represented by the following constitutional repeat-
ing units: –C6H4C(O)C6H4C(O)C6H3I– (3) and
–C6H4C(O)C6H3C(O)I– (4).
Unlike bromobenzene, the reaction of acetyl iodide
with 1,4-dibromobenzene afforded exclusively
1,4-diiodobenzene (yield 74%) and acetyl bromide
(Scheme 2).
Scheme 2.
The data of stationary ESR showed that oligomers
3 and 4 are fairly similar to polymers isolated pre-
viously in the photolysis of acetyl iodide in benzene or
toluene [2]. They exhibited pronounced paramagnetic
properties. Their ESR spectra in the g-factor region
displayed sharp asymmetric signals typical of free
radicals. The upper part of the ESR lines conforms to
the Lorentz shape, and the lower part, to the Gauss
curve, which suggests their irregular structure. The
concentration of paramagnetic centers amounts to
1019 spin/g (Table 1). However, the g-factors charac-
terizing the contribution of spin–orbit interactions were
appreciably different (∆g = 0.00045). The electric con-
ductivity of oligomers 3 and 4 is lower by an order of
magnitude than that of the polymers isolated previ-
ously [2], despite a high iodine content. Presumably,
unlike the polymers described in [2] which were doped
with iodine, iodine atoms in 3 and 4 are covalently
bound to macromolecules. The concentration of un-
paired electrons and signal width (less than 10 G) in
the ESR spectra of 3 and 4 (which characterize en-
vironment of paramagnetic centers) make it possible to
record spin echo in the pulsed mode at room tempera-
ture and determine relaxation parameters T1 and T2.
The spin–spin relaxation time T2 was much shorter
than the spin–lattice relaxation time T1, which is
typical of dilute paramagnetics [3]. The relaxation time
of 3 and 4 is determined by two contributions, which
indicates a complicated character of interaction be-
tween unpaired electrons and their environment and
requires special study.
Br
O
2
+
Me
I
Br
I
O
hν
2
+
Me
Br
I
Ultraviolet irradiation of a mixture of acetyl iodide
and fluorobenzene or hexafluorobenzene gave neither
halogen exchange products nor biacetyl. These
findings indicated that fluorine-substituted benzenes
inhibit photochemical generation of radicals and their
subsequent reactions.
No iodobenzene was formed in the photolysis of
benzoyl iodide in chloro- or bromobenzene. Here, the
initial halobenzene remained unchanged, whereas
benzoyl iodide was converted into black oligomers 3
(in chlorobenzene) and 4 (in bromobenzene) whose
compositions were estimated at C20H11O2I and
C14H7O2I, respectively.
The elemental compositions of 3 and 4 and their IR
spectra which contained absorption bands at 1688 and
Table 1. Electric conductivities, parameters of ESR spectra,
and relaxation parameters of polymers 3 and 4
Parameter
σ, S/cm
3
4
2.8×10–9
1.8×1019
7.40
1.3×10–8
1.9×1019
7.30
N, spin/g
ΔH, G
Polymeric products 5–10 were also obtained by UV
irradiation of mixtures of acetyl iodide with bromo-
arenes (2- and 3-bromotoluenes and 4-bromo-1,2-di-
methylbenzene). No biacetyl was detected in the reac-
tion mixtures. According to the data of elemental
analysis and IR spectroscopy, polymers 5–10 lack
carbonyl group. This means that acylation of the
aromatic ring does not occur, as in the photolysis of
acetyl iodide in halobenzenes. Compounds 5–10 are
formed as a result of photochemical polycondensation
of intermediate iodo-substituted arenes generated in
g-Factor
2.00497
0.80
2.00542
0.77
Asymmetry factor
A/B
T1,a ns
T1′
T1″
T2′
T2″
2940.0
8913.0
–
858.8
3720.2
T2,a ns
00002.61
0126.4
0132.5
a
Spin–lattice relaxation time T1 and spin–spin relaxation time T2
characterize the lifetime of an electron spin in the excited state.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 1 2013

PHOTOCHEMICAL REACTIONS OF ACYL IODIDES WITH ARYL HALIDES
19
the first step of the photochemical process via halogen
exchange in the initial bromoarenes (Scheme 3).
start to decompose (10% weight loss) at 330–420°C
against 255–318°C for 5, 7, and 9. Samples 5–8
obtained by the photochemical reactions of acetyl
iodide with o- and m-bromotoluenes showed similar
thermal stabilities (up to 200–235°C). Polymers 9 and
10 synthesized from acetyl iodide and 4-bromo-1,2-
dimethylbenzene were more thermally stable, and they
began to decompose at a temperature higher by 118–
120°C than that found for polymers 5–8.
Scheme 3.
nMeC(O)I
+
nBrC6H5 – mMem
hν
hν
[nIC6H5 – mMem]
H[C6H5 – mMem]nI
–nMeC(O)Br
–(n – 1)HI
n = 1, 2: m = 1, 2.
The results of ESR study of polymers 5–10 and
their electric conductivities are given in Table 2. It is
seen that compounds 5–10 are semiconductors. Their
ESR parameters are very similar. Polymers 5–10
exhibit pronounced paramagnetic properties and are
characterized by narrow, almost symmetric ESR
signals typical of free radicals. The line shape is either
mixed or approaching the Lorentz shape. The concen-
tration of paramagnetic centers was estimated at
1019 spin/g. All polymers obtained after 50-h irradia-
tion showed narrower ESR signals and increased con-
centration of paramagnetic centers with simultaneous
reduction of the conductivity. Thus not all paramag-
netic centers generated by irradiation ensure electric
conductivity.
Increase of the UV irradiation time in the reaction
of acetyl iodide with bromoarenes leads to reduced
concentration of iodine in the polymeric products,
presumably due to profound polycondensation. In the
reaction of acetyl iodide with 2- or 3-bromotoluene
increase of the irradiation time from 20 to 50 h
changes the polymer composition from C13H13I (5) to
C45H42I (6) and from C15H14I (7) to C30H26I (8).
Analogous propagation of the polyarylene chain was
observed in the photolysis of acetyl iodide in 4-bromo-
1,2-dimethylbenzene. In this case, the resulting
polymers had the compositions C32H34I (9, 20 h) and
C55H41I (10, 50 h). Polymers 5–10 were isolated as
black nonfusible powders which were insoluble in
water and common organic solvents. According to the
differential thermal analysis data, polymers 5–10 are
stable up to 200–320°C. All compounds 5–10 are
characterized by gradual lowering of the weight loss
curves on heating to 900°C, and in all cases a weak
exothermic effect was observed at 88–90°C, presum-
ably due to elimination of iodine. These data indicate
that variation of the conditions, namely increase of the
UV irradiation time from 20 to 50 h, leads to formation
of more thermally stable polymers 6, 8, and 10 which
Unlike acetyl iodide, the photolysis of benzoyl
iodide in 2- and 3-bromotoluene gave benzil as the
only product as a result of combination of benzoyl
radicals (Scheme 4).
To conclude, we have demonstrated the possibility
for using acyl iodides in photochemical reactions with
haloarenes to obtain iodoarenes and iodine-containing
oligomers and polymers possessing paramagnetic and
semiconducting properties. Our results confirm once
Table 2. Parameters of the ESR spectra and electric conductivities of polymers 5–10
Compound
no.
Asymmetry
factor A/B
Electric conductivity,
S/cm
Reactants, reaction time g-Factor ∆H, G N, spin/g
Line shape
Mixed
05
06
07
08
09
10
MeCOI–o-bromotoluene, 2.0031
7.1 1.4×1019
6.3 9.4×1018
6.0 3.0×1019
5.3 2.0×1019
5.2 2.8×1019
5.0 3.5×1019
0.96
0.99
1.00
1.02
1.02
1.00
1.5×10–9
3.6×10–10
7.1×10–8
1.7×10–11
1.7×10–9
7.1×10–10
20 h
MeCOI–m-bromotoluene, 2.0028
Mixed
Mixed
20 h
MeCOI–o-bromotoluene, 2.0028
50 h
MeCOI–m-bromotoluene, 2.0024
Mixed, closer
to Lorentz
50 h
MeCOI–4-bromo-1,2-di-
methylbenzene, 20 h
2.0024
2.0026
Close to purely
Lorentz
MeCOI–4-bromo-1,2-di-
methylbenzene, 50 h
Mixed, closer
to Lorentz
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 1 2013

VORONKOV et al.
Reaction of acetyl iodide with bromobenzene.
20
Scheme 4.
O
A mixture of 8.5 g (50 mmol) of acetyl iodide and
7.9 g (50 mmol) of bromobenzene was irradiated with
UV light over a period of 50 h. Distillation of the mix-
ture under atmospheric pressure gave 20% of acetyl
bromide, bp 78–79°C, nD20 = 1.4520 (bp 75–77°C, nD20 =
1.450 [11]), 9% of iodobenzene, and 16% of biacetyl.
The solid residue was washed with acetone and diethyl
ether to obtain polymer 2. Found, %: C 58.8; H 3.1;
I 37.8. C16H13I. Calculated, %: C 57.8; H 3.9; I 38.2.
O
hν
Ph
2
Ph
–I2
Ph
I
O
more a wide synthetic potential of acyl iodides as
reagents and synthons in organic synthesis [4–7]. In
addition, appreciable dependence of the reaction path
on the arene and acyl iodide nature has been observed
in their photochemical transformations (cf. [2]).
Photolysis of benzoyl iodide in chlorobenzene.
A mixture of 11.6 g (50 mmol) of benzoyl iodide and
5.6 g (50 mmol) of chlorobenzene was irradiated with
UV light over a period of 50 h. After removal of
chlorobenzene by distillation, the residue was washed
with acetone and diethyl ether and dried in a vacuum
desiccator. The product was powder-like nonfusible
polymer 3 which was insoluble in water and common
organic solvents. IR spectrum, ν, cm–1: 3070, 3016
(C–Harom), 1686 (C=O), 1601, 1452, 1418 (C–Carom),
932, 707, 682 (δC–Harom), 545 (C–I), 430 (δC–C).
Found, %: C 56.7; H 2.7; I 31.1. C20H11O2I. Calcu-
lated, %: C 58.5; H 2.7; I 30.9.
EXPERIMENTAL
Photochemical reactions were carried out under
irradiation with an OKN-11 mercury lamp. The IR
spectra were recorded on a UR-20 spectrometer from
thin films. The ESR spectra were obtained on
a Radiopan SE/X-2547 spectrometer equipped with
a magnetometer and a high-frequency meter (sensitiv-
ity 5×1010 spin/g, room temperature), as well as on
a Bruker Elexsys E-580 radiospectrometer in conti-
nuous and pulsed modes at room temperature. The
concentrations of paramagnetic centers were calculated
according to the procedure described in [8] using
DPPH as calibration standard and nomogram for
double integration of the first derivative curve [9]. The
relaxation times T1 and T2 were determined with the
aid of the following pulse sequences: π-T-π/2-τ-π for
T1 and π/2-τ-π for T2, where π/2 = 20 ns, τ = 200 ns,
and T = 1000 ns [10]. Thermogravimetric analysis was
performed on a MOM Q-1500 derivatograph
(Hungary) in air (maximal temperature 900°C, heating
rate 10 deg/min; DTA sensitivity 1/10).
Photolysis of benzoyl iodide in bromobenzene.
A mixture of 11.6 g (50 mmol) of benzoyl iodide and
7.9 g (50 mmol) of bromobenzene was irradiated with
UV light over a period of 50 h. Distillation of the mix-
ture under atmospheric pressure gave initial bromoben-
zene. The residue was treated as described above to
isolate polymer 4 whose properties were similar to
those of 3. IR spectrum, ν, cm–1: 3070, 3023 (C–Harom),
1688 (C=O), 1602, 1453, 1423 (C–Carom), 934, 707,
683 (δC–Harom), 551 (C–I), 430 (δC–C). Found, %:
C 49.1; H 2.6; I 37.3. C14H7O2I. Calculated, %: C 50.3;
H 2.1; I 38.2.
Reaction of acetyl iodide with chlorobenzene.
A mixture of 8.5 g (50 mmol) of acetyl iodide and
5.6 g (50 mmol) of chlorobenzene was irradiated with
UV light over a period of 29 h. Distillation of the mix-
ture under atmospheric pressure gave 25% of acetyl
Photolysis of acetyl iodide in 2-bromotoluene.
A mixture of 8.5 g (50 mmol) of acetyl iodide and
8.6 g (50 mmol) of 2-bromotoluene was irradiated with
UV light over a period of 20 h. Distillation of the
mixture gave acetyl bromide. The residue was washed
with acetone and diethyl ether and dried in a vacuum
desiccator to isolate black powder-like polymeric
product 5. IR spectrum, ν, cm–1: 3436 (C–Harom), 2920,
2853 (C–Haliph), 1627, 1434 (C–Carom), 1027, 868, 728
(δC–H), 618 (C–I), 463 (δC–C). Found, %: C 52.12;
H 4.45; I 42.74. C13H13I. Calculated, %: C 52.70;
H 4.39; I 42.94.
chloride, bp 50–51°C, nD20 = 1.389 (bp 52°C, nD20
=
1.389 [11]); 14% of biacetyl, bp 88–89°C, nD20 = 1.3950
(bp 88, nD20 = 1.3950 [11]); and 8% of iodobenzene,
bp 186–187°C, nD20 = 1.6200 (bp 188°C, nD20 = 1.6200
[11]). Found, %: I 63.17. C6H5I. Calculated, %:
I 62.20.
After distillation of liquid products, the residue was
washed with acetone and dried in a vacuum desiccator
to obtain black nonfusible polymer 1, which was
insoluble in water and common organic solvents.
Found, %: C 81.4; H 5.1; I 11.3; C/H ratio 1.5.
C78H53I. Calculated, %: C 83.8; H 4.7; I 11.4.
Irradiation of a mixture of the same amounts of
acetyl iodide and 2-bromotoluene over a period of
50 h, followed by distillation of acetyl bromide, gave
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 1 2013

PHOTOCHEMICAL REACTIONS OF ACYL IODIDES WITH ARYL HALIDES
21
polymeric product 6 whose properties were similar to
those of 5. IR spectrum, ν, cm–1: 3436 (C–Harom), 2918,
2850 (C–Haliph), 1628, 1440 (C–Carom), 1029, 867, 728
(δC–H), 587 (C–I), 463 (δC–C). Found, %: C 75.47;
H 5.57; I 15.89. C45H42I. Calculated, %: C 76.16;
H 5.92; I 17.91.
(δC–C). Found, %: C 79.89; H 5.06; I 15.35. C55H41I.
Calculated, %: C 79.71; H 4.95; I 15.33.
Photolysis of benzoyl iodide in 2-bromotoluene.
Irradiation with UV light of a mixture of 11.6 g
(50 mmol) of benzoyl iodide and 8.6 g (50 mmol) of
o-bromotoluene over a period of 24 h gave 55% of
benzil, mp 99–100°C (95–96°C [2]). IR spectrum:
ν 1687 cm–1 (C=O) (cf. 1681 cm–1 [12]). Likewise,
53% of benzil was isolated after UV irradiation of
a mixture of benzoyl iodide and m-bromotoluene over
a period of 24 h.
Photolysis of acetyl iodide in 3-bromotoluene.
A mixture of 8.5 g (50 mmol) of acetyl iodide and 8.6 g
(50 mmol) of 3-bromotoluene was irradiated with UV
light over a period of 20 h. Distillation of the mixture
gave acetyl bromide and unreacted acetyl iodide and
3-bromotoluene (28–30% of the initial amount). The
residue was washed with acetone and diethyl ether to
obtain black powder-like polymeric product 7. IR
spectrum, ν, cm–1: 3440 (C–Harom), 2910, 2851
(C–Haliph), 1625, 1439 (C–Carom), 1030, 863, 729
(δC–H), 587 (C–I), 464 (δC–C). Found, %: C 56.07;
H 4.6; I 42.49. C15H14I. Calculated, %: C 56.07;
H 4.36; I 39.56.
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Likewise, after irradiation of a mixture of 17 g
(100 mmol) of acetyl iodide and 17.2 g (100 mmol) of
2-bromotoluene over a period of 50 h, we isolated
polymer 8 whose properties were similar to those of 7.
IR spectrum, ν, cm–1: 3440 (C–Harom), 2918, 2852
(C–Haliph), 1587, 1424 (C–Carom), 1038, 865, 759
(δC–H), 528 (C–I), 448 (δC–C). Found, %: C 72.93;
H 4.88; I 25.30. C30H26I. Calculated, %: C 70.17;
H 5.06; I 24.75.
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methylbenzene. A mixture of 8.5 g (50 mmol) of
acetyl iodide and 9.3 g (50 mmol) of 4-bromo-1,2-
dimethylbenzene was irradiated with UV light over
a period of 20 h. Distillation of the mixture gave acetyl
bromide and unreacted acetyl iodide and 4-bromo-1,2-
dimethylbenzene. The solid residue was washed with
acetone and diethyl ether to obtain polymeric product 9
whose properties were similar to those of 5–8. IR spec-
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1591, 1444 (C–Carom), 1019, 867, 812 (δC–H), 528
(C–I), 442 (δ C–C). Found, %: C 69.72; H 5.74;
I 20.64. C32H34I. Calculated, %: C 70.45; H 6.23;
I 23.30.
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Irradiation of a mixture of the same amounts of the
reactants over a period of 50 h gave polymeric product
10 which was analogous to 9. IR spectrum, ν, cm–1:
3428 (C–Harom), 2915, 2852 (C–Haliph), 1576, 1442
(C–Carom), 996, 864, 808 (δC–H), 512 (C–I), 437
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 1 2013