SYNTHESIS OF POLYCHLORINATED MONO- AND BISIMIDES
217
N-[6-(Maleimido)hexyl]imide of endo,exo-2,3,4,5-
tetrachlorobicyclo[4.4.0]deca-2,4-diene-8,9-dicarbox-
ylic acid (XLI). Yield 90%, mp 152°С, Rf 0.58. IR spec-
trum, ν, cm–1: 1720, 1780 (С=О), 1601 (С=С), 680–720
(С–Сl). Found, %: C 50.43; H 3.91; Cl 26.89; N 4.88.
М 519.28. С22H22Cl4N2O4. Calculated, %: C 50.79;
H 4.25; Cl 27.26; N 5.38. М 520.20.
tained from bisimide XLIV. Yield 94%. mp 328–330°С,
Rf 0.75, η 0.28 dL g–1. IR spectrum, ν, cm–1 1712, 1780
(С=О), 1608 (С=С), 600–750 (С–Сl). Found, %: C 57.28;
H 3.01; N 4.21; Cl 22.98. С29H20Cl4N2O4.1 Calculated,
%: C 57.83; H 3.34; N 4.65; Cl 23.54.
REFERENCES
N-[4-(Maleimido)phenyl]imide of endo,exo-
2,3,4,5-tetrachlorobicyclo[4.4.0]deca-2,4-diene-
8,9-dicarboxylic acid (XLII). Yield 92%, mp 166°С,
Rf 0.62. IR spectrum, ν, cm–1: 1720, 1778 (С=О),
1600 (С=С), 680–720 (С–Сl). Found, %: C 51.11;
H 2.28; Cl 27.31; N 5.11. М 512. С22H14Cl4N2O4.
Calculated, %: C 51.60; H 2.75; Cl 27.70; N 5.46.
М 512.14.
1. Korshak, V.V., Khimicheskoe stroenie i temperaturnye
kharakteristiki polymerov (Chemical Structure and Thermal
Parameters of Polymers), Moscow: Nauka, 1970.
2. Korshak, V.V., Rusanov, A.L., Margalitadze, Yu.N., and
Tabidze, R.S., Plast. Massy, 1987, no. 5, p. 5.
3. Kodolov, V.I., Goryuchest’ i ognestoikost’ polymernykh
materialov (Сombustibility and Fire Resistance), Moscow:
Khimiya, 1976.
N-{4-[4-(Maleimido)benzyl]phenyl}imide of
endo,exo-2,3,4,5-tetrachlorobicyclo[4.4.0]deca-2,4-
diene-8,9-dicarboxylic acid (XLIII). Yield 94%, mp
202°С, Rf 0.63. IR spectrum, ν, cm–1: 1720, 1780 (С=О),
1602 (С=С), 670–750 (С–Сl). Found, %: C 57.48; H 3.00;
Cl 23.29; N 4.12. М 623. С29H20Cl4N2O4. Calculated, %:
C 59.07; H 3.83; Cl 22.49; N 4.44. М 630.31.
4. Salakhov, M.S. and Guseinov, M.M., J. Chem. Tech., 1978,
p. 44.
5. Zul’faliev, Sh.R., Salakhov, M.S., Pirgulieva, M.S.,
and Musaeva, N.F., Abstracts of Papers, Vses. Nauchn.
Konf. “Sovremennoe sostoyanie i perspektivy razvitiya
teoreticheskikh osnov proizvodstva chloroorganicheskikh
produktov” (All-Union Conf. “Contemporary State and
Prospectivity of Developing Theoretical Principles of Pro-
duction of Chlororganic Products”), Baku, 1991, p. 195.
6. Salakhov, M.S., Guseinov, M.M., Musaeva, N.E., and
Alekperov, N.A., USSR Inventor’s Certificate 467070; SSSR
Byull. Izobr., 1975, no. 14.
7. Zul’faliev, Sh.R., Salakhov, M.S., Pirgulieva, M.S. and
Efendiev, A.A., Azerb. Khim. Zh., 1998, no. 3, p. 27
8. Salakhov, M.S, Umaeva, V.S., and Alikhanova, A.I.,
Abstract of Papers, Konferentsiya posvyashchennaya
100-letiyu akad. M.F.Nagieva (Conference Dedicated to
the 100th Anniversary of M.F. Nagiev), 2008, p. 143.
9. Salakhov, M.S., Timosheva, A.P., Vul’fson, S.G., Sala-
khova, R.S., Musaeva, N.E., Alekperov, N.A., and Veresh-
chagin, A.N., Russ. Chem. Bull., 1975, p. 785.
10. Salakhov, M.S., Alekperov, N.A., Poladov, P.M., Salak-
hova, Ya.S., Guseinov, M.M., and Kucherov, V.F., Zh. Org.
Khim., 1973, vol. 11, p. 942.
11. Kazitsyna, L.A. and Kupletskaya, N.B., Primenenie UF,
IK, YaMR i mass-spektroskopii v organicheskoi khimii
(Application of UV, IR, NMR and Mass Spectroscopy in
Organic Chemistry), Moscow: Izd. Mosk. Gos. Univ., 1978.
12. Nekrasov, V.V., Rukovodstvo k malomu praktikumu po
organicheskoi khimii (Handbook for Small Practicum on
Organic Chemistry), Moscow: Khimiya, 1964.
N-{4-[4-(Maleimido)-2-methoxybenzyl]-
2-methoxyphenyl}imide endo,exo-2,3,4,5-tet-
ra-chlorobicyclo[4.4.0]deca-2,4-diene-8,9-di-
carboxylic acid (XLIV). Yield 91%, mp 215°С,
Rf 0.64. IR spectrum, ν, cm–1: 1720, 1780 (С=О), 1602
(С=С), 670–750 (С–Сl). Found, %: C 55.79; H 3.18;
Cl 20.98; N 3.85. М 632. С31H24Cl4N2O6. Calculated, %:
C 56.19; H 3.62; Cl 21.45; N 4.23. М 630.31.
Poly[4,8,9,10-tetrachlorohexahydro-4,8-
ethenopyrrolo[3,4-f]isoindole-1,3,5,7-tetraone-
alt-1,1'-methanediyldibenzene] (LV). A mixture of
0.05 mol of bisimide XXXVIII and 0.05 g of hydro-
quinone in 20 mL of anhydrous DMAA was stirred
for 6 h at 140°С. On cooling the reaction mixture was
poured into ice water. The precipitated crystals were
filtered off, washed with water, dried, and recrystal-
lized from methanol. Yield 92%, mp 304–315°С,
Rf 0.71. Intrinsic viscosity (DMF, 25°С) η 0.22 dL g–1.
IR spectrum, ν, cm–1: 1710, 1780 (С=О), 1610 (С=С),
680–750 (С–Сl). Found, %: C 54.28; H 2.01; N 4.96;
Cl 25.62. С25H14Cl4N2O4. Calculated, %: C 54.77; H 2.57;
N 5.10; Cl 25.80.
Poly[4,10,11,12-tetrachlorodecahydro-4,10-
ethenopyrrolo[5,6-f]isoindole-1,3,6,8-tetraone-
alt-1,1’- methanediyldibenzene] (LVI) was similarly ob-
13. Akhrem, A.A. and Kuznetsova, A.I., Tonkosloinaya khro-
______________
1 Molecular weight of the monomer unit of the polymer.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 2 2014