Alkylation of aromatic compounds with adamantan-1-ol

Article abstract of DOI:10.1134/S1070428007040082

Reactions of substituted benzenes, naphthalenes, and 2- and 3-phenyl-1-benzofurans with adamantan-1-ol in trifluoroacetic acid lead to the formation of the corresponding mono-and diadamantylsubstituted aromatic compounds. Nauka/Interperiodica 2007.

Full text of DOI:10.1134/S1070428007040082

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2007, Vol. 43, No. 4, pp. 538–543. © Pleiades Publishing, Ltd., 2007.
Original Russian Text © A.V. Stepakov, A.P. Molchanov, R.R. Kostikov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 4,
pp. 540–544.
Alkylation of Aromatic Compounds with Adamantan-1-ol
A. V. Stepakov, A. P. Molchanov, and R. R. Kostikov
St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504 Russia
Received March 22, 2006
Abstract—Reactions of substituted benzenes, naphthalenes, and 2- and 3-phenyl-1-benzofurans with
adamantan-1-ol in trifluoroacetic acid lead to the formation of the corresponding mono- and diadamantyl-
substituted aromatic compounds.
DOI: 10.1134/S1070428007040082
Extensive studies in the field of adamantane chem-
istry are related to wide prospects in using adamantane
derivatives in the synthesis of biologically active com-
pounds, heat-resistant polymers, and oil and fuel addi-
tives [1–3]. Adamantane derivatives are well known as
antiviral and antimicrobial agents with a broad spec-
trum of activity [4–6]; some of these compounds can
be used in the treatment of diseases of nervous system
[7, 8]. Adamantylation of aromatic hydrocarbons leads
to compounds that are convenient starting materials in
target-oriented organic synthesis [9–11]. One of the
main procedures for the introduction of an adamantyl
group into an aromatic ring is based on reactions of
halogenated adamantanes with arenes in the presence
of Lewis acids [12–18]. The use of hydroxy-substi-
tuted adamantanes in the alkylation of aromatic hydro-
carbons ensures the process to occur under milder con-
ditions. These reactions are carried out in strong protic
acids [19]; phosphoric anhydride was also used as
catalyst [20]. Kovalev and Shokova [21] reported on
the alkylation of aromatic hydrocarbons with 1-ada-
mantyl trifluoroacetate prepared from 1-bromoada-
mantane and trifluoroacetic acid. Reactions of adaman-
tan-1-ol with substituted olefins in trifluoroacetic acid
were shown to produce the corresponding 1-(1-ada-
mantyl)alkan-1-ols [22]. Alkylation of calix[n]arenes
(n = 4–6) with adamantan-1-ol in trifluoroacetic was
also described [23].
In the present work we examined reactions of some
benzene and naphthalene derivatives, as well as of
2- and 3-phenyl-1-benzofurans with adamantan-1-ol in
trifluoroacetic acid. o-Xylene (Ia) and 1,2,3,4-tetra-
hydronaphthalene (IIa) reacted with admantan-1-ol in
trifluoroacetic acid at room temperature to give
1-(1-adamantyl)-3,4-dimethylbenzene (IIa) and
6-(1-adamantyl)-1,2,3,4-tetrahydronaphthalene (IIb) in
84 and 72% yield, respectively. The melting points and
spectral parameters of compounds IIa and IIb coin-
cided with those reported in [24, 25]. The alkylation of
phenol (Ic), o-methylphenol (Id), resorcinol (Ie), and
4-chloro-3-methylphenol (If) under analogous condi-
tions afforded the corresponding adamantyl-substituted
phenols IIc–IIf in high yields (Scheme 1). The melting
points and spectral parameters of compounds IIc–IIe
coincided with published data [15, 16, 18], and the
corresponding data for IIf are given in Exsperimental.
The reactions of 2-methyl-, 2-hydroxy-, 1,3-di-
methyl-, 2,3-dihydroxy-, and 2-methoxynaphthalenes
Scheme 1.
R1
R1
R2
R2
CF3COOH
+
OH
R3
Ia–If
R3
IIa–IIf
R1 = R2 = Me, R3 = H (a); R1R2 = (CH2)4, R3 = H (b); R1 = R3 = H, R2 = HO (c); R1 = Me, R2 = HO, R3 = H (d); R1 = R3 = H,
R2 = R3 = HO (e); R1 = Cl, R2 = Me, R3 = HO (f).
538

ALKYLATION OF AROMATIC COMPOUNDS WITH ADAMANTAN-1-OL
539
Scheme 2.
R1
R2
R3
R1
R4
R2
R3
CF3COOH
IVa–IVe
+
OH
R4
IIIa–IIIh
R1
Va–Vc
III, IV, R1 = R3 = R4 = H, R2 = Me (a), HO (b); R1 = R3 = H, R2 = R4 = Me (c); R1 = R4 = H, R2 = R3 = HO (d); R1 = R3 = R4 = H,
R2 = MeO (e); R1 = HO, R2 = R3 = R4 = H (f); R1 = MeO, R2 = R3 = R4 = H (g); R1 = Me, R2 = R3 = R4 = H (h); V, R1 = HO (a),
MeO (b), Me (c).
IIIa–IIIe with adamantan-1-ol in trifluoroacetic acid
gave monoadamantyl-substituted naphthalenes IVa–
IVe (Scheme 2). The new substituent entered the
6-position in IIIa, IIIb, IIId, and IIIe and the 7-posi-
tion in IIIc, as followed from the spectral parameters.
The properties of compounds IVa, IVb, and IVe
coincided with those reported in [18, 21, 26], and the
melting points and spectral parameters of newly syn-
thesized compounds IVc and IVd are given in Experi-
mental.
signals in the region δ 1.5–2.2 ppm (30H) from protons
in the adamantyl substituents and signals from aromat-
ic protons, δ, ppm: Va: 6.94 s, 7.18 s, 7.97 s, 7.51 d,
7.71 d (J = 8.2 Hz); Vb: 6.90 s, 7.31 s, 8.11 s, 7.57 d,
7.74 d (J = 8.4 Hz); Vc: 7.57 s, 7.78 s, 8.07 s, 7.67 d,
7.99 d (J = 9.7 Hz).
We also examined alkylation of 2- and 3-phenyl-
1-benzofurans VIa and VIb with 1-adamantan-1-ol in
trifluoroacetic acid. The reaction involved both
aromatic rings in molecules VIa and VIb and gave
diadamantyl-substituted derivatives VII and VIII
(Scheme 3). The alkylation of 3-phenyl-1-benzofuran
(VIa) was accompanied by considerable tarring of the
reaction mixture, and adamantyl-substituted benzo-
The alkylation of 1-substituted naphthalenes IIIf–
IIIh with adamantan-1-ol resulted in the formation of
the corresponding 3,7-diadamantyl derivatives Va–Vc
(Scheme 2). The 1H NMR spectra of Va–Vc contained
Scheme 3.
R = Ph, R' = H
R
O
CF3COOH
+
VII
R'
OH
O
VIa, VIb
R = H, R' = Ph
O
VIII
R = Ph, R' = H (a); R = H, R' = Ph (b).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 4 2007

STEPAKOV et al.
540
furan VII was isolated in 22% yield by treatment of
the mixture with methanol–acetone. Compound VII
displayed in the H NMR spectrum signals at δ 1.7–
and the precipitate was filtered off, washed with a so-
lution of sodium carbonate, dried, and recrystallized
from ethanol. Yield 0.95 g (84%), mp 110–112°C; pub-
lished data [13]: mp 99–112°C. IR spectrum, ν, cm–1:
1110, 1140, 1240, 1320, 1340, 1460, 1520, 1610,
2910 s. H NMR spectrum, δ, ppm (J, Hz): 1.77–2.11
(15H, Ad), 2.21 s (3H, Me), 2.25 s (3H, Me), 7.20 d
(1H, Harom, J = 8.2), 7.24 s (1H, Harom), 7.27 d (1H,
1
2.0 ppm (30H) from protons in the adamantyl frag-
ments, a singlet at δ 7.5 ppm from 2-H, signals at
δ 7.2 and 7.1 ppm (d, J = 7.9 Hz) from 7-H and 6-H,
respectively, and signals from the para-substituted
benzene ring at δ 7.38 and 7.42 ppm (d, J = 8.2 Hz).
In the 13C NMR spectrum of VII, strong signals at δC
128.3 and 131.3 ppm were observed due to equivalent
carbon nuclei in the para-substituted benzene ring.
1
Harom, J = 8.2).
Compounds IIb–IIf were synthesized in a similar
way.
The alkylation of 2-phenyl-1-benzofuran (VIb) led
to a product (yield 56%) which was assigned the struc-
ture of 5-(1-adamantyl)-2-[4-(1-adamantylphenyl)]-1-
benzofuran (VIII) on the basis of its 1H and 13C NMR
6-(1-Adamantyl)-1,2,3,4-tetrahydronaphthalene
(IIb) was obtained from 0.17 g (1.3 mmol) of 1,2,3,4-
tetrahydronaphthalene (Ib) and 0.2 g (1.3 mmol) of
adamantan-1-ol in 4 ml of trifluoroacetic acid. Yield
0.26 g (72%), mp 76–78°C (from MeOH); published
data [25]: mp 78–80°C. UV spectrum (ethanol):
λmax 279 nm (logε 3.78). IR spectrum, ν, cm–1: 970,
990, 1040, 1110, 1240, 1320, 1350, 1460, 1540, 1620,
1
spectra. The H NMR spectrum of VIII contained
signals from adamantane protons (δ 1.8–2.2 ppm,
30H), 3-H (δ 7.2 ppm, s), 7-H and 6-H (δ 7.4 and
7.3 ppm, d, respectively, J = 7.7 Hz), and aromatic
protons (δ 7.46 and 7.90 ppm, d, J = 8.0 Hz). Equiv-
alent carbon atoms in the para-substituted benzene
ring gave strong peaks at δC 125.1 and 129.2 ppm.
1
2920 s. H NMR spectrum, δ, ppm (J, Hz): 1.66–2.11
(19H, Ad, CH2), 2.71–2.82 m (4H, CH2), 7.15 d (1H,
H
arom, J = 8.2), 7.23 d (1H, Harom, J = 8.2), 7.30 s
(1H, Harom).
4-(1-Adamantyl)phenol (IIc) was obtained from
Thus our results demonstrated that the reaction of
adamantan-1-ol with aromatic compounds in trifluoro-
acetic acid provides a convenient procedure for the
synthesis of adamantyl-substituted derivatives.
0.12 g (1.3 mmol) of phenol (Ic) and 0.2 g (1.3 mmol)
of adamantan-1-ol in 4 ml of trifluoroacetic acid. Yield
0.23 g (79%), mp 180–182°C (from EtOH); published
1
EXPERIMENTAL
data [16]: mp 181–183°C. H NMR spectrum, δ, ppm
(J, Hz): 1.17–2.03 (15H, Ad), 6.98 d (2H, Harom, J =
7.2), 7.12 d (2H, Harom, J = 7.2), 9.11 br.s (1H, OH).
The elemental compositions were determined on
a Hewlett–Packard 185-B CHN analyzer. The melting
points were determined on a Boetius melting point
apparatus. The IR spectra were recorded from 2%
solutions in chloroform on a UR-20 spectrometer. The
1H and 13C NMR spectra were measured on a Bruker
DPX-300 instrument (300 and 75 MHz, respectively)
from 2% solutions in CDCl3 (compounds IVa, IVc–
IVe, Vb, VII, VIII), DMSO-d6 (IIc–IIf, IVb, Va), or
benzene-d6 (IIa, IIb, Vc). The UV spectra were ob-
tained in dichloroethane on a Specord UV-Vis spectro-
photometer. The purity of the products was checked,
and the progress of reactions was monitored, by TLC
on Silufol UV-254 plates. Adamantan-1-ol was synthe-
sized by the procedure described in [21].
4-(1-Adamantyl)-2-methylphenol (IId) was ob-
tained from 0.2 g (1.8 mmol) of 2-methylphenol (Id)
and 0.27 g (1.8 mmol) of adamantan-1-ol in 4 ml
of trifluoroacetic acid. Yield 0.35 g (81%), mp 138–
139°C (from EtOH); published data [18]: mp 138–
139°C. IR spectrum, ν, cm–1: 1120, 1240, 1320, 1340,
1460, 1520, 1600, 2920 s, 3590. 1H NMR spectrum, δ,
ppm (J, Hz): 1.17–2.02 (15H, Ad), 2.10 s (3H, Me),
6.68 d (1H, Harom, J = 8.2), 6.93 d (1H, Harom, J = 8.2),
7.01 s (1H, Harom), 8.97 br.s (1H, OH).
4-(1-Adamantyl)benzene-1,3-diol (IIe) was ob-
tained from 0.2 g (1.8 mmol) of resorcinol (Ie) and
0.27 g (1.8 mmol) of adamantan-1-ol in 4 ml of tri-
fluoroacetic acid. Yield 0.34 g (76%), mp 233–235°C
(from EtOH); published data [15]: mp 235–236°C. IR
spectrum, ν, cm–1: 970, 1120, 1240, 1340, 1450, 1510,
1-(1-Adamantyl)-3,4-dimethylbenzene (IIa).
Adamantan-1-ol, 0.72 g (4.7 mmol), was added under
stirring to a solution of 0.5 g (4.7 mmol) of o-xylene
(Ia) in 5 ml of trifluoroacetic acid, and a solid material
began to separated from the solution almost imme-
diately. The mixture was diluted with 30 ml of water,
1
2920, 3600. H NMR spectrum, δ, ppm (J, Hz): 1.70–
2.00 (15H, Ad), 6.12 d (1H, Harom, J = 8.3), 6.22 s (1H,
Harom), 6.80 d (1H, Harom, J = 8.3), 8.92 s (1H, OH),
9.01 s (1H, OH).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 4 2007

ALKYLATION OF AROMATIC COMPOUNDS WITH ADAMANTAN-1-OL
541
J = 8.9), 7.83 s (1H, Harom). Found, %: C 90.74;
H 8.96. C22H26. Calculated, %: C 90.98; H 9.02.
2-(1-Adamantyl)-3-chloro-4-methylphenol (IIf)
was obtained from 0.09 g (0.63 mmol) of 3-chloro-4-
methylphenol (If) and 0.1 g (0.66 mmol) of ada-
mantan-1-ol in 3 ml of trifluoroacetic acid. Yield 0.1 g
(59%), mp 153–155°C. IR spectrum, ν, cm–1: 890, 980,
1060, 1110, 1150, 1240, 1320, 1350, 1390, 1460, 1510,
6-(1-Adamantyl)naphthalene-2,3-diol (IVd) was
obtained from 0.21 g (1.3 mmol) of naphthalene-2,3-
diol (IIId) and 0.2 g (1.3 mmol) of adamantan-1-ol in
6 ml of trifluoroacetic acid. Yield 0.3 g (78%),
mp 210–212°C (from EtOH–H2O). IR spectrum, ν,
cm–1: 870, 890, 1120, 1250, 1270, 1320, 1350, 1460,
1520, 1630, 2920 s, 3550, 3590. 1H NMR spectrum, δ,
ppm (J, Hz): 1.83–2.15 (15H, Ad), 5.62 br.s (2H, OH),
7.19 s (1H, Harom), 7.21 s (1H, Harom), 7.42 d (1H,
1
1610, 2930 s, 3590. H NMR spectrum, δ, ppm: 1.71–
2.02 (15H, Ad), 2.31 s (3H, Me), 6.70 s (1H, Harom),
6.96 s (1H, Harom), 9.39 br.s (1H, OH.). Found, %:
C 73.35; H 7.53. C17H21ClO. Calculated, %: C 73.77;
H 7.65.
H
arom, J = 9.1), 7.53 s (1H, Harom), 7.61 d (1H, Harom,
6-(1-Adamantyl)-2-methylnaphthalene (IVa).
Adamantan-1-ol, 0.32 g (2.1 mmol), was added under
stirring to a solution of 0.3 g (2.1 mmol) of 2-methyl-
naphthalene (IIIa) in 6 ml of trifluoroacetic acid. The
mixture was kept for 12 h at room temperature and
diluted with water, and the precipitate was filtered off,
washed with a solution of sodium carbonate, dried, and
recrystallized from ethanol. Yield 0.56 g (82%). IR
spectrum, ν, cm–1: 880, 980, 1040, 1110, 1114, 1240,
1320, 1450, 1530, 1610, 2910 s. 1H NMR spectrum, δ,
ppm (J, Hz): 1.84–2.17 (15H, Ad), 2.52 s (3H, Me),
7.31 d (1H, Harom, J = 8.4), 7.56 d (1H, Harom, J = 8.4),
7.59 s (1H, Harom), 7.70 d (1H, Harom, J = 8.4), 7.72 s
(1H, Harom), 7.75 d (1H, Harom, J = 8.4). Found, %:
C 91.18; H 8.77. C21H24. Calculated, %: C 91.25;
H 8.75.
J = 9.1). Found, %: C 81.23; H 7.47. C20H22O2. Cal-
culated, %: C 81.60; H 7.53.
6-(1-Adamantyl)-2-methoxynaphthalene (IVe)
was obtained from 0.5 g (3.16 mmol) of 2-methoxy-
naphthalene (IIIe) and 0.48 g (3.16 mmol) of ada-
mantan-1-ol in 8 ml of trifluoroacetic acid. Yield
0.71 g (77%), mp 143–145°C; published data [21]:
mp 143–144.5°C. UV spectrum (dichloroethane), λmax
,
nm (logε): 263 (3.82), 272 (3.81), 320 (3.29), 333
(3.40). IR spectrum, ν, cm–1: 860, 890, 930, 980, 1040,
1130, 1170, 1270, 1340, 1390, 1460, 1490, 1510,
1620, 2920 s. H NMR spectrum, δ, ppm (J, Hz):
1.84–2.16 (15H, Ad), 3.94 s (3H, OMe), 7.13 s (1H,
1
Harom), 7.15 d (1H, Harom, J = 8.2), 7.57 d (1H, Harom
J = 8.2), 7.68 s (1H, Harom), 7.72 d (1H, Harom, J = 8.2),
,
7.75 d (1H, Harom, J = 8.2).
Compounds IVb–IVe were synthesized in a similar
way.
3,7-Bis(1-adamantyl)naphthalen-1-ol (Va). A so-
lution of 0.12 g (0.83 mmol) of naphthalen-1-ol (IIIf)
in 4 ml of trifluoroacetic acid was added under stirring
to a solution of 0.3 g (1.97 mmol) of adamantan-1-ol in
2 ml of trifluoroacetic acid. A solid began to separate
from the resulting solution in a few minutes. The mix-
ture was kept for 16 h at room temperature and diluted
with 30 ml of water, and the precipitate was filtered
off, washed with a solution of sodium carbonate, dried,
and recrystallized from isopropyl alcohol. Yield 0.23 g
6-(1-Adamantyl)naphthalen-2-ol (IVb) was ob-
tained from 0.3 g (2.1 mmol) of naphthalen-2-ol (IIIb)
and 0.32 g (2.1 mmol) of adamantan-1-ol in 6 ml of
trifluoroacetic acid. Yield 0.43 g (73%), mp 193–
195°C (from EtOH); published data [18]: mp 194–
195°C. IR spectrum, ν, cm–1: 1150, 1240, 1320, 1450,
1
1540, 1620, 2920 s, 3590. H NMR spectrum, δ, ppm
(J, Hz): 1.76–2.08 (15H, Ad), 7.04 d (1H, Harom, J =
8.2), 7.06 s (1H, Harom), 7.48 d (1Harom, J = 8.2), 7.60 d
(1H, Harom, J = 8.2), 7.63 s (1H, Harom), 7.72 d (1H,
1
(67%), mp 345–350°C. H NMR spectrum, δ, ppm
(J, Hz): 1.76–2.12 (30H, Ad), 6.94 s (1H, Harom), 7.18 s
(1H, Harom), 7.51 d (1H, Harom, J = 8.2), 7.71 d (1H,
Harom, J = 8.2), 7.97 s (1H, Harom), 9.53 br.s (1H, OH).
Found, %: C 87.52; H 8.60. C30H36O. Calculated, %:
C 87.33; H 8.79.
H
arom, J = 8.2), 9.56 br.s (1H, OH).
7-(1-Adamantyl)-1,3-dimethylnaphthalene (IVc)
was obtained from 0.4 g (2.56 mmol) of 1,3-dimethyl-
naphthalene (IIIc) and 0.39 g (2.56 mmol) of adaman-
tan-1-ol in 7 ml of trifluoroacetic acid. Yield 0.64 g
λmax, nm (logε): 283 (3.79), 312 (2.97), 320 (2.72), 326
(2.92). IR spectrum, ν, cm–1: 880, 980, 1040, 1110,
1240, 1320, 1450, 1540, 1620, 2990 s. H NMR spec-
trum, δ, ppm (J, Hz): 1.85–2.18 (15H, Ad), 2.48 s (3H,
Me), 2.70 s (3H, Me), 7.17 s (1H, Harom), 7.47 s (1H,
Harom), 7.57 d (1H, Harom, J = 8.9), 7.76 d (1H, Harom
Compounds Vb and Vc were synthesized in a simi-
lar way.
1
3,7-Bis(1-adamantyl)-1-methoxynaphthalene
(Vb) was obtained from 0.2 g (1.3 mmol) of adaman-
tan-1-ol and 0.1 g (0.63 mmol) of 1-methoxynaphtha-
lene (IIIg) in 7 ml of trifluoroacetic acid. Yield 0.22 g
,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 4 2007

STEPAKOV et al.
542
(81%), mp 293–295°C (from octane). UV spectrum
(dichloroethane), λmax, nm (logε): 293 (3.70), 312
(3.47), 323 (3.30). IR spectrum, ν, cm–1: 880, 980,
1010, 1120, 1290, 1320, 1400, 1460, 1580, 1600,
2910 s. H NMR spectrum, δ, ppm (J, Hz): 1.84–2.16
(30H, Ad), 4.05 s (3H, OMe), 6.90 s (1H, Harom), 7.31 s
to separate from the solution. The mixture was kept for
8 h at room temperature and diluted with water, and
the precipitate was filtered off, washed with a solution
of sodium carbonate, dried, and recrystallized twice
from ethanol–ethyl acetate. Yield 0.23 g (56%). IR
spectrum, ν, cm–1: 990, 1030, 1050, 1110, 1240, 1320,
1
1
(1H, Harom), 7.57 d (1H, Harom, J = 8.4), 7.74 d (1H,
1350, 1400, 1450, 1490, 1610, 2910 s. H NMR spec-
H
arom, J = 8.4), 8.11 s (1H, Harom). Found, %: C 87.41;
trum, δ, ppm (J, Hz): 1.83–2.20 (30H, Ad), 7.20 s (1H,
3-H), 7.29 d (1H, Harom, J = 7.7), 7.31 s (1H, Harom),
7.36 d (1H, Harom, J = 7.7), 7.46 d (2H, Harom, J = 8.0),
7.90 d (2H, Harom, J = 8.2). 13C NMR spectrum, δC,
ppm: 29.5, 29.6, 37.2, 37.3, 37.5, 38.3, 42.8, 44.0
(Ad); 102.6 (C3); 106.0, 116.4, 124.0, 125.1, 128.5,
129.2, 131.3, 144.0, 148.6, 154.3 (Carom); 156.6 (C2).
Found, %: C 88.22; H 8.13. C34H38O. Calculated, %:
C 88.26; H 8.28.
H 8.71. C31H38O. Calculated, %: C 87.27; H 8.98.
3,7-Bis(1-adamantyl)-1-methylnaphthalene (Vc)
was obtained from 0.3 g (1.97 mmol) of adamantan-1-
ol and 0.12 g (0.84 mmol) of 1-methylnaphthalene
(IIIh) in 6 ml of trifluoroacetic acid. Yield 0.32 g
(92%), mp 302–303°C (from toluene). UV spectrum
1
(dichloroethane): λmax 280 nm (logε 3.79). H NMR
spectrum, δ, ppm (J, Hz): 1.86–2.16 (30H, Ad), 2.77 s
(3H, Me), 7.57 s (1H, Harom), 7.67 d (1H, Harom, J =
9.7), 7.78 s (1H, Harom), 7.99 d (1H, Harom, J = 9.7),
8.07 s (1H, Harom). Found, %: C 90.58; H 9.21. C31H38.
Calculated, %: C 90.67; H 9.33.
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2910 s. H NMR spectrum, δ, ppm (J, Hz): 1.68–2.12
(30H, Ad), 7.09 d (1H, Harom, J = 7.9), 7.22 d (1H,
Harom, J = 7.9), 7.38 d (2H, Harom, J = 8.2), 7.42 d (2H,
H
arom, J = 8.2), 7.43 s (1H, Harom), 7.49 s (1H, 2-H).
13C NMR spectrum, δC, ppm: 28.7, 29.5, 36.8, 37.1,
37.3, 41.9, 44.1 (Ad); 107.3, 115.7, 119.2, 119.8
(Carom); 127.5 (C3); 128.3, 129.9, 131.3, 134.8 (Carom);
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fluoroacetic acid. After several minutes, a solid began
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 4 2007

ALKYLATION OF AROMATIC COMPOUNDS WITH ADAMANTAN-1-OL
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