1-[(E)-2-(5-Benzyloxy-2-nitrophenyl)vinyl]pyrrolidine (2b), mp 96–97°C. 1H NMR spectrum, , ppm
(J, Hz): 7.75 (1H, d, J = 12.1, H Ar); 7.25 (6H, m, H Ar); 6.9 (2H, m, H Ar + CH=); 5.20 (1H, d, J = 12.1,
CH=); 5.00 (2H, s, CH2); 3.10 (4H, m, CH2 pyrrolidine); 1.80 (4H, m, CH2 pyrrolidine).
1-[(E)-2-(5-Isopropoxy-2-nitrophenyl)vinyl]pyrrolidine (2c) crystallized upon maintenance for 24 h
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at 0°C; mp 59–60°C. H NMR spectrum, , ppm (J, Hz): 7.95 (1H, d, J = 8.0, H Ar); 7.20 (1H, d, J = 11.2,
H Ar); 6.85 (1H, s, H Ar); 6.50 (1H, d, J = 8.5, CH=); 6.05 (1H, d, J = 11.2, CH=); 4.65 (1H, q, J = 6.0, CH);
3.35 (4H, m, CH2 pyrrolidine); 1.95 (4H, m, CH2 pyrrolidine); 1.45 (6H, d, J = 6.0, CH3).
1-{(E)-2-[5-(4-Fluorobenzyl)oxy-2-nitrophenyl]vinyl}pyrrolidine (2d) crystallized upon maintenance
for 24 h at 0°C; mp 93–94°C. 1H NMR spectrum, , ppm (J, Hz): 7.54 (3H, m, H Ar); 7.13 (2H, m, H Ar); 6.80
(1H, m, H Ar); 6.75 (1H, d, J = 8.4, CH=); 6.61 (1H, m, H Ar); 6.05 (1H, d, J = 11.1, CH=); 5.05 (2H, s, CH2);
3.39 (4H, m, CH2 pyrrolidine); 2.10 (4H, m, CH2 pyrrolidine). 19F NMR spectrum, , ppm: –115.8 (1F, s).
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1-{(E)-2-[5-(3,4-Dichlorobenzyl)oxy]-2-nitrophenyl]vinyl}pyrrolidine (2e), mp 68–70°C. H NMR
spectrum, , ppm (J, Hz): 7.90 (1H, d, J = 7.5, H Ar); 7.50 (2H, m, H Ar); 7.30 (2H, m, H Ar); 6.90 (1H, s,
H Ar), 6.50 (1H, m, CH=); 6.00 (1H, d, J = 11.2, CH=); 5.05 (2H, s, CH2); 3.35 (4H, m, CH2 pyrrolidine); 2.00
(4H, m, CH2 pyrrolidine).
1-[(E)-2-(2-Chloro-6-nitrophenyl)vinyl]pyrrolidine (2f) was obtained as a viscous, noncrystalline oil;
bp 111°C (0.03 mmHg) [4]. Decomposes at higher pressure. The purity of the sample, as indicated by 1H NMR
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spectroscopy, was 70%. The sample was used without further purification. H NMR spectrum, , ppm (J, Hz):
8.2 (1H, m, H Ar); 7.35 (2H, m, H Ar); 6.7 (1H, d, J = 9.0, CH=); 5.2 (1H, d, J = 9.0, CH=); 3.4 (4H, m,
CH2 pyrrolidine); 2.1 (4H, m, CH2 pyrrolidine).
2,5-Dimethyl-1-{3-nitro-4-[(E)-2-pyrrolidin-1-ylvinyl]phenyl}-1H-pyrrole (2g), mp 103–105°C (de-
1
comp.). H NMR spectrum, , ppm (J, Hz): 7.80 (1H, s, H Ar); 7.55 (2H, d, J = 11.0, H Ar); 7.45 (1H, d,
J = 16.0, CH=); 5.90 (3H, s, =CH + CH pyrrole); 3.4 (4H, m, CH2 pyrrolidine); 2.10 (6H, s, CH3); 2.00 (4H, m,
CH2 pyrrolidine).
(E)-2-(5-Difluoromethoxy-2-nitrophenyl)-N,N-dimethylethyleneamine (2h), mp 65–68°C. The cor-
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responding derivative with pyrrolidine is liquid at room temperature. H NMR spectrum, , ppm (J, Hz): 7.90
(1H, d, J = 9.2, H Ar); 7.10 (1H, s, H Ar); 6.95 (1H, d, J = 9.2, H Ar); 6.65 (1H, d, J = 13.8, CH=); 6.57 (1H, t,
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J = 72.8, HCF2); 5.90 (1H, d, J = 13.8, CH=); 2.95 (6H, s, N(CH3)2). F NMR spectrum, , ppm (J, Hz): –82.2
(2F, d, J = 74.0).
1-{(E)-2-[5-(2,2-Difluoroethoxy)-2-nitrophenyl]vinyl}pyrrolidine (2i), mp 128–129°C. 1H NMR
spectrum, , ppm (J, Hz): 7.95 (1H, d, J = 10.0, H Ar); 7.25 (1H, m, CH=); 6.87 (1H, m, H Ar); 6.48 (1H, m,
H Ar); 6.12 (1H, tm, J1 = 57.0, HCF2); 6.05 (1H, m, CH=); 4.23 (2H, td, J1 = 12.9, J2 = 3.9, CH2CHF2); 3.35
(4H, m, CH2 pyrrolidine); 1.96 (4H, m, CH2 pyrrolidine). 19F NMR spectrum, , ppm (J, Hz): –126.2 (2F, dt,
J1 = 56.0, J2 = 14.2).
1-{(E)-2-[2-Nitro-5-(2,2,3,3-tetrafluoropropoxy)phenyl]vinyl}pyrrolidine (2j), mp 106–107°C. 1H
NMR spectrum, , ppm (J, Hz): 7.95 (1H, d, J = 9.2, H Ar); 7.25 (1H, d, J = 13.1, CH=); 6.87 (1H, s, H Ar);
6.47 (1H, m, H Ar); 6.3–5.8 (2H, m, CH= + CHF2); 4.40 (2H, t, J = 11.2, CH2F2); 3.35 (4H, m, CH2 pyr-
rolidine), 1.96 (4H, m, CH2 pyrrolidine). 19F NMR spectrum, , ppm (J, Hz): –125.6 (2F, s); –139.7 (2F, d,
J = 54.4).
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1-[(E)-2-(4-Methyl-2-nitrophenyl)vinyl]pyrrolidine (2k), mp 69–70°C. H NMR spectrum, , ppm
(J, Hz): 7.70 (1H, s, H Ar); 7.35 (1H, m, H Ar); 7.20 (2H, m, HAr + CH=); 5.80 (1H, d, J = 12.0, CH=); 3.30
(4H, m, CH2 pyrrolidine); 2.30 (3H, s, CH3); 2.00 (4H, m, CH2 pyrrolidine).
1-[(E)-2-[4-Methoxy-2-nitrophenyl)vinyl]pyrrolidine (2l) was obtained as a dark-red semiliquid at
room temperature, which precipitates as crystals from cold methanol and may be separated by filtration on an
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ice-cooled funnel. H NMR spectrum, , ppm (J, Hz): 7.40 (2H, m, H Ar); 7.10 (1H, d, J = 12.2, CH=); 6.95
(1H, m, H Ar); 5.85 (1H, d, J = 12.2, CH=); 3.80 (3H, s, OCH3); 3.35 (4H, m, CH2 pyrrolidine); 1.95 (4H, m,
CH2 pyrrolidine).
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