OLEINIK et al.
928
Initial substituted salicylaldehydes Ia–If and 4-tri-
phenylmethylaniline were synthesized according to the
procedures described in [6, 7].
(IIe). Yield 86%, mp 153–155°C. IR spectrum:
1
ν 1618 cm–1 (N=CH). H NMR spectrum, δ, ppm:
1.37 s (9H, t-Bu), 1.64 s (6H, Me), 6.80–7.35 m (26H,
H
arom), 8.47 s (1H, CH=N), 13.34 s (1H, OH). Found,
Substituted salicylaldehyde imines IIa–IIf (gen-
eral procedure). A 5-ml ampule was charged with
a mixture of 0.5 mmol of salicylaldehyde Ia–If and
0.17 g (0.5 mmol) of 4-triphenylmethylaniline. The
ampule was sealed, placed into a hermetically closed
Teflon container, and heated in an LG MS-1724W
microwave oven over a period of 10 min at a power of
500 W. The solid products were purified by recrystal-
lization from methanol.
%: C 87.80; H 7.16; N 2.34. C45H43NO. Calculated, %:
C 88.05; H 7.06; N 2.28.
2-tert-Butyl-4-triphenylmethyl-6-[(4-triphenyl-
methylphenylimino)methyl]phenol (IIf). Yield 78%,
mp 150–152°C. IR spectrum: ν 1618 cm–1 (N=CH).
1H NMR spectrum, δ, ppm: 1.27 s (9H, t-Bu), 6.90–
7.40 m (36H, Harom), 8.35 s (1H, CH=N), 13.50 s (1H,
OH). Found, %: C 89.20; H 6.52; N 1.73. C55H47NO.
Calculated, %: C 89.51; H 6.42; N 1.90.
2-[Dimethyl(phenyl)methyl]-4-methyl-6-[(4-tri-
phenylmethylphenylimino)methyl]phenol (IIa).
Yield 91%, mp 175–177°C. IR spectrum: ν 1620 cm–1
The IR spectra were recorded in KBr on a Bruker
1
Vector 22 spectrometer. The H NMR spectra were
1
(N=CH). H NMR spectrum, δ, ppm: 1.73 s (6H, Me),
measured from solutions in CCl4 on a Bruker WP-
200 SY instrument at 200.13 MHz using hexamethyl-
disiloxane as internal reference. The progress of reac-
tions and the purity of products were monitored by
TLC on Silufol UV-254 plates using chloroform as
eluent. The elemental composition of compound IIa
was determined from the high-resolution mass spec-
trum obtained on a Finnigan MAT-8200 mass spec-
trometer. The elemental compositions of IIb–IIf were
determined using a Carlo Erba 1106 CHN analyzer.
2.35 s (3H, 4-CH3), 6.85–7.28 m (26H, Harom),
8.50 s (1H, CH=N), 12.97 s (1H, OH). Found:
[M]+ 571.28673. C42H37NO. Calculated: M 571.28750.
4-tret-Butyl-2-[dimethyl(phenyl)methyl]-6-[(4-
triphenylmethylphenylimino)methyl]phenol (IIb).
Yield 93%, mp 95–98°C. IR spectrum: ν 1619 cm–1
1
(N=CH). H NMR spectrum, δ, ppm: 1.31 s (9H,
t-Bu), 1.73 s (6H, Me), 6.98–7.45 m (26H, Harom),
8.52 s (1H, CH=N), 12.95 s (1H, OH). Found, %:
C 87.58; H 7.09; N 2.18. C45H43NO. Calculated, %:
C 88.05; H 7.06; N 2.28.
REFERENCES
2,4-Bis[dimethyl(phenyl)methyl]-6-[(4-triphenyl-
methylphenylimino)methyl]phenol (IIc). Yield 96%,
mp 109–111°C. IR spectrum: ν 1618 cm–1 (N=CH).
1H NMR spectrum, δ, ppm: 1.66 s (12H, Me), 6.81–
7.30 m (31H, Harom), 8.43 s (1H, CH=N), 12.96 s (1H,
OH). Found, %: C 88.76; H 7.03; N 1.92. C50H45NO.
Calculated, %: C 88.85; H 6.71; N 2.07.
1. Makio, H., Kashiwa, N., and Fujita, T., Adv. Synth.
Catal., 2002, vol. 344, p. 477.
2. Ivanchev, S.S., Usp. Khim., 2007, vol. 76, p. 669.
3. Oleinik, I.I., Oleinik, I.V., Zhilovskii, G.S., Ivan-
chev, S.S., and Tolstikov, G.A., Russ. J. Org. Chem.,
2007, vol. 43, p. 1671.
4. Oleinik, I.I., Oleinik, I.V., Ivanchev, S.S., and Tolsti-
kov, G.A., Russ. J. Org. Chem., 2005, vol. 41, p. 1329.
2-[Dimethyl(phenyl)methyl]-4-triphenylmethyl-
6-[(4-triphenylmethylphenylimino)methyl]phenol
(IId). Yield 75%, mp 122–124°C. IR spectrum:
5. Rakhmankulov, D.L., Bikbulatov, I.Kh., Shulaev, N.S.,
and Shavshukova, S.Yu., Mikrovolnovoe izluchenie i
intensifikatsiya khimicheskikh protsessov (Microwave
Irradiation and Intensification of Chemical Processes),
Moscow: Khimiya, 2003.
6. Kochnev, A.I., Oleinik, I.I., Oleinik, I.V., Ivanchev, S.S.,
and Tolstikov, G.A., Izv. Ross. Akad. Nauk, Ser. Khim.,
2007, p. 1084.
1
ν 1617 cm–1 (N=CH). H NMR spectrum, δ, ppm:
1.55 s (6H, Me), 6.90–7.27 m (41H, Harom), 8.33 s (1H,
CH=N), 13.15 s (1H, OH). Found, %: C 90.01; H 6.48;
N 1.56. C60H49NO. Calculated, %: C 90.08; H 6.17;
N 1.75.
2-tert-Butyl-4-[dimethyl(phenyl)methyl]-6-
7. Zimmermann, T.J. and Müller, T.J.J., Synthesis, 2002,
[(4-triphenylmethylphenylimino)methyl]phenol
p. 1157.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 44 No. 6 2008