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A. Orzeszko et al. · Novel Imides and Thioimides with Chiral Aliphatic Tails
N-Alkyltrimellitimides (11-13): Trimellitimides with N- 2.06 (m, 11 H, CH2), 3.78 (t, 2 H, OCH2), 4.00 (t, 2 H,
butyl, N-hexyl and N-nonyl substituents were synthesized NCH2), 6.96 – 7.00 (m, 2 H), 7.30 (m, 2 H), 7.50 – 7.66 (m,
according to the well known and patented method from 4 H), 7.99 (m, 1 Himide), 8.55 – 8.67 (m, 2 Himide); calcd.
trimellitic anhydride and proper amines in dry boiling C 76.13, H 7.77, N 2.40; found C 76.19, H 7.76, N 2.36.
DMF [18].
N-Alkyl-4-[(S)-4’-citronellylbiphenyl-4’-yl)oxycarbonyl]-
15: Yield 32%; FT-IR (CH2Cl2): ν = 1777 (C=Oimide),
1741 (C=Oester), 1736 (C=Oimide); 1H NMR (200 MHz,
CDCl3): δ = 0.96 – 1.03 (m, 12 H, CH3), 1.58 – 2.06 (m,
15 H, CH2), 3.75 (t, 2 H, OCH2), 4.01 (t, 2 H, NCH2), 6.96 –
7.00 (m, 2 H), 7.30 (m, 2 H), 7.50 – 7.64 (m, 4 H), 7.99 (m,
1 Himide), 8.55 – 8.67 (m, 2 Himide); calcd. C 77.07, H 7.46,
N 2.40; found C 77.17, H 7.49, N 2.32.
phthalimide (14-16): The general procedure of obtaining
compounds 14-16 were frequently published in the literature
[6 – 10]. The synthesis was carried out from mesogenic units
10 and proper N-alkyltrimellitimides 11-13 in methylene
chloride using dicyclohexylcarbodiimide (DCC) and DMAP
as catalyst. The crude products of interest were crystallised
from a benzene/methanol mixture and then the crystals were
purified by means of flash-column chromatography (SiO2)
using chloroform/methanol (20:1) as an eluent.
16: Yield 34%; (CH2Cl2): ν = 1776 (C=Oimide), 1741
(C=Oester), 1735 (C=Oimide) cm−1 1H NMR (200 MHz,
;
CDCl3): δ = 0.96 – 1.03 (m, 12 H, CH3), 1.56 – 2.09 (m,
21 H, CH2), 3.75 (t, 2 H, OCH2), 4.01 (t, 2 H, NCH2), 6.96 –
7.00 (m, 2 H), 7.30 (m, 2 H), 7.50 – 7.64 (m, 4 H), 7.99 (m,
1 Himide), 8.55 – 8.67 (m, 2 Himide); calcd. C 77.15, H 8.48,
N 2.14; found C 77.17, H 8.49, N 2.10.
14: Yield 28%; FT-IR (CH2Cl2): ν = 1776 (C=Oimide),
1742 (C=Oester), 1736 (C=Oimide
) ;
cm−1 1H NMR
(200 MHz, CDCl3): δ = 0.96 – 1.08 (m, 12 H, CH3), 1.59 –
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