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NIGMATULLIN et al.
reactor was opened at 85°C, and oligomeric product
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3
a–3d was filtered off (Table 1). The filtrate was
1
2
. Tibaoui, T., Ayachi, S., Hamidi, M., Bouachrine, M.,
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va, N.A., Gazizov, A.R., Tagirov, L.R., Klochkov, V.V.,
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cooled to room temperature, and compound 4 pre-
cipitated. The bottom layer of the reaction mixture
(
aqueous alkaline solution) was neutralized to pH 7
with 0.1 N aqueous HCl, and the black solid was fil-
tered off and washed with distilled water.
4
,4′-(Ethane-1,2-diylidene)bis(2,6-di-tert-butyl-
cyclohexa-2,5-dien-1-one) (1). Reaction temperature
9
1
stirring speed 1400 rpm [15]. Yield 99%, mp 315°C.
IR spectrum, ν, cm : 3003 (C–Harom), 2952, 2909,
3
4
. Furlani, A., Russo, M.V., and Cataldo, F., Synth. Met.,
–1
0°C, reaction time 90 min, oxygen flow rate 300 h ,
0% sodium hydroxide, solvent kerosene (50 mL),
1
989, vol. 29, no. 1, p. 507.
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and Liogon’kii, B.I., Vysokomol. Soedin., 1972, vol. 14,
no. 6, p. 1395.
–
1
2
1
865 (Me), 1640, 1605 (C=Carom), 1605 (C=O), 1600,
454 (C=Carom), 1360, 1256 (t-Bu). H NMR spectrum
5. Zhang, A.J., He, J., Guan, Y., Li, Z.Y., Zhang, Y.J., and
1
Zhu, J.X., Sci. China: Chem., 2012, vol. 55, p. 5.
(
DMSO-d , 600 MHz), δ, ppm: 1.42 s (36H, t-Bu),
6. Yamamoto, K., Asada, T., Nishide, H., and Tsushida, E.,
6
6
.54 s (2H, =CH), 7.19 s (4H, Harom). Found, %:
Bull. Chem. Soc. Jpn., 1990, vol. 63, no. 4, p. 1211.
C 82.80, 82.56; H 9.73. C H O . Calculated, %:
7. Wang, P., Martin, B.D., Parida, S., Rethwisch, D.G., and
Dordick, J.S., J. Am. Chem. Soc., 1995, vol. 117, no. 51,
p. 12885.
8. Berlin, A.A., Ragimov, A.V., Sadykh-Zade, S.I.,
Gadzhieva, T.A., and Takhmazov, B.M., Vysokomol.
Soedin., 1975, vol. 17, no. 1, p. 111.
3
0
42
2
C 82.55; H 10.15.
Polypyrocatechol (3a). Yield 86%. IR spectrum, ν,
–
1
cm : 3600 (OH), 1600, 1512 (C=Carom), 1350, 1250,
180 (C–OH).
Polyhydroquinone (3b). Yield 89%. IR spectrum,
1
9
. Yamamoto, T. and Kimura, T., Macromolecules, 2011,
–
1
ν, cm : 3150 (OH), 1590, 1510 (C=Carom) 1352, 1350,
185 (C–OH).
Poly-1,2-benzoquinone (3c). Yield 80%. IR spec-
vol. 44, no. 7, p. 2245.
0. Sabaa, M.W., Madkour, T.M., and Yassin, A.A., Polym.
Degrad. Stab., 1988, vol. 22, p. 195.
11. Akhmadullin, R.M. and Akhmadullina, A.G., RU Patent
no. 2552516, 2015.
1
1
–
1
trum, ν, cm : 3200 (OH), 1595 (C=O), 1557, 1262
(
C=C), 1262 (C–C), 740 (δCH).
1
2. Akhmadullin, R.M., Gatiyatullin, D.R., Akhmadulli-
na, A.G., Verizhnikov, L.V., and Mukmeneva, N.A.,
Vestn. Kazan. Tekhnol. Univ., 2014, vol. 17, no. 6,
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3. Bonn, C.R. and Compbell, T.W., J. Org. Chem., 1957,
vol. 22, no. 4, p. 458.
4. Ragimov, A.V., Bektashi, F.T., and Liogon’kii, B.I.,
Poly-1,4-benzoquinone (3d). Yield 85%. IR spec-
–
1
trum, ν, cm : 3400 (OH), 1592 (C=O), 1450, 1358
C=C), 1119 (C–C), 1050, 800 (δC–H). Found, %:
C 67.9; H 1.88. Calculated, %: C 64.24; H 2.81.
,4′-[(E)-Ethene-1,2-diyl]bis(2,6-di-tert-butyl-
phenol) (4). Yield 98%, light yellow material,
(
1
1
4
–
1
mp 214°C. IR spectrum, ν, cm : 3627, 3607 (O–H),
003 (C–Harom), 2952, 2909, 2865 (Me), 1437, 1420
C=Carom), 1360, 1256 (t-Bu), 1231, 1133 (C–OH),
60, 730, 660 (δC–Harom).
Vysokomol. Soedin., 1975, vol. 17, no. 12, p. 2753.
3
(
9
15. Hoang, H.Y., Akhmadullin, R.M., Akhmadullina, F.Yu.,
Zakirov, R.K., Akhmadullina, A.G., and Gazizov, A.S.,
Russ. J. Org. Chem., 2018, vol. 54, p. 1008.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 54 No. 9 2018