Condensation of N-(2-vinyloxyethyl)ethane-1,2-diamine with carbonyl compounds

Article abstract of DOI:10.1134/S107042801004007X

Condensation of N-(2-vinyloxyethyl)ethane-1,2-diamine with aromatic aldehydes gave mixtures of 2-aryl-1-(2-vinyloxyethyl)imidazolidines and N-arylmethylidene-N′-(2-vinyloxyethyl)ethane-1,2-diamines in an overall yield of 79-84%, while analogous condensati

Full text of DOI:10.1134/S107042801004007X

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2010, Vol. 46, No. 4, pp. 495–498. © Pleiades Publishing, Ltd., 2010.
Original Russian Text © B.F. Kukharev, V.K. Stankevich, N.A. Lobanova, G.R. Klimenko, V.V. Stankevich, E.V. Bragin, 2010, published in Zhurnal
Organicheskoi Khimii, 2010, Vol. 46, No. 4, pp. 505–508.
Condensation of N-(2-Vinyloxyethyl)ethane-1,2-diamine
with Carbonyl Compounds
B. F. Kukharev, V. K. Stankevich, N. A. Lobanova, G. R. Klimenko,
V. V. Stankevich, and E. V. Bragin
Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
e-mail: irk_inst_chem@irioch.irk.ru
Received June 1, 2009
Abstract—Condensation of N-(2-vinyloxyethyl)ethane-1,2-diamine with aromatic aldehydes gave mixtures of
2-aryl-1-(2-vinyloxyethyl)imidazolidines and N-arylmethylidene-N′-(2-vinyloxyethyl)ethane-1,2-diamines in
an overall yield of 79–84%, while analogous condensation with cyclic and acyclic ketones resulted in the
formation of only the corresponding Schiff bases (yield 53–83%).
DOI: 10.1134/S107042801004007X
It is known that 2-vinyloxyethylamines possessing
a primary amino group, as other typical primary
amines, react with carbonyl compounds, yielding the
corresponding Schiff bases [1]. However, the reaction
of N-(2-vinyloxyethyl)ethane-1,2-diamine (I) with
acetaldehyde, leading to 2-methyl-1-(2-vinyloxyethyl)-
imidazolidine in 97% yield, is the only reported ex-
ample of such condensation with participation of com-
pound I [2]. On the other hand, only condensations of
N,N′-disubstituted ethane-1,2-diamines with carbonyl
compounds give individual imidazolidines [3], while
monosubstituted ethylenediamines could give rise to
mixtures of imidazolidines and Schiff bases.
the condensations of diamine I with ketones IId–IIf,
Schiff bases IVd–IVf were obtained as the only prod-
ucts (Scheme 1).
Schiff bases IV were characterized by absorption
bands in the region 1640–1665 cm–1 [ν(C=N)] in the
1
IR spectra. The H NMR spectra of compounds IVa–
IVc contained a singlet from the N=CH proton at
δ 8.30–8.36 ppm, indicating the presence of only one
E isomer (cf. [4]). In the 13C NMR spectra of IVa–IVf,
the N=CH carbon signal was located at δC 158.88–
1
163.68 ppm. The H NMR spectra of the products
obtained from diamine I and ketones IId–IIf lacked
signals assignable to protons in the NCHN group,
while protons in the vinyloxy group appeared as three
doublets of doublets at δ 3.94–3.97 (cis-CH=), 4.13–
4.17 (trans-CH=), and 6.42–6.44 ppm (OCH=); these
data showed the absence of imidazolidines among the
products.
In the present work we studied condensation of di-
amine I with various carbonyl compounds. The reac-
tions were carried out by heating equimolar mixtures
of the reactants in boiling benzene with simultaneous
removal of water as azeotrope. Unlike acetaldehyde,
the condensation of diamine I with aromatic aldehydes
IIa–IIc led to the formation of 18–62% of Schiff bases
IVa–IVc together with imidazolidines IIIa–IIIc. In
Imidazolidines IIIa–IIIc obtained by condensation
of diamine I with aldehydes IIa–IIc displayed in the
1H NMR spectra a singlet from the NCHN proton at
Scheme 1.
R
O
H2C
H
H
N
O
N
R
NH
N
+
+
O
NH2
O
N
R'
–H2O
H2C
H2C
R
R'
IIa–IIf
R'
I
IIIa–IIIc
IVa–IVf
R = H, R′ = Ph (a), pyridin-4-yl (b), pyridin-3-yl (c); RR′ = (CH2)4 (d), (CH2)5 (e); R = Me, R′ = Me2CHCH2 (f).
495

KUKHAREV et al.
496
Scheme 2.
H
N
CH2
H2C
I
+
CH2O
O
N
O
N
NH
H2C
CH2
O
N
H
N
H2C
CH2
O
N
N
O
N
N
H
H
V
δ 4.16–4.22 ppm. In addition, protons in the vinyloxy
group resonated as three multiplets resulting from
superposition of doublets of doublets belonging to
vinyl protons in Schiff bases IVa–IVc and imidazoli-
dines IIIa–IIIc. The ratios of compounds IV and III,
determined from the intensities of the N=CH and
NCHN signals, were 1 : 0.59 (IVa : IIIa), 1 : 4.52
(IVb:IIIb), and 1:1.99 (IVc:IIIc).
δC 75.32 ppm, i.e., in a considerably stronger field than
did C2 in imidazolidine derivatives. In addition, no
signals assignable to CH2=N group were observed in
the 1H and 13C NMR spectra of V.
EXPERIMENTAL
1
The H and 13C NMR spectra were recorded at
26°C on a Bruker DPX-400 spectrometer at 400 and
100 MHz, respectively, from solutions in CDCl3 using
hexamethyldisiloxane as internal reference. The IR
spectra were measured from thin films on a Specord
75IR spectrophotometer. The purity of the initial
reactants and products was checked by GLC on
an LKhM-80 chromatograph equipped with a thermal
conductivity detector and a steel column, 3×3000 mm,
packed with 3% of OV-17 on Inerton Super (0.160–
0.200 mm); oven temperature programming from 60 to
280°C at a rate of 4 deg/min; carrier gas helium.
In the reaction of diamine I with methyl isobutyl
ketone (IId) we obtained Schiff base IVd as a mixture
of E and Z isomers, the latter prevailing. According to
the intensities of signals from protons in methyl groups
(singlets at δ 1.76 and 1.80 ppm), the ratio of the Z and
E isomers was 1.0:0.12. Signals from all other groups
were overlapped almost completely by each other, so
that it was difficult to determine the corresponding
coupling constants.
Our results do not conform completely to the
existing views on electronic effects in heterolytic intra-
molecular cyclizations [5]. In keeping with these
views, the addition of more nucleophilic NH group to
C=N bond should occur more readily than the addition
of OH group. Moreover, increased electrophilicity of
the C=N carbon atom favors formation of the cyclic
product. The condensations of 2-amino alcohols with
carbonyl compounds follow the above rules: aromatic
aldehydes give rise to imino alcohols, while cyclic
products (oxazolidines) are obtained from aliphatic
ketones [6]. Presumably, the observed deviation from
general rules is related to elongation of the substituent
on the nitrogen atom, which in some cases destabilizes
cyclic structure [5].
Commercial carbonyl compounds and N-(2-vinyl-
oxyethyl)ethane-1,2-diamine (I) prepared according to
the procedure described in [2] (its purity was no less
than 97% according to the GLC data) were distilled
just before use.
Condensation of N-(2-vinyloxyethyl)ethane-1,2-
diamine (I) with carbonyl compounds IIa–IIf (gen-
eral procedure). A mixture of 6.51 g (0.05 mol) of
N-(2-vinyloxyethyl)ethane-1,2-diamine (I), 0.05 mol
of carbonyl compound IIa–IIf, and 100 ml of benzene
was heated under reflux in a flask equipped with
a Dean–Stark trap until water no longer separated. The
products were isolated from the reaction mixture by
vacuum distillation.
The only product formed in the condensation of
diamine I with formaldehyde was 1,3,5-tris[2-(2-vinyl-
oxyethylamino)ethyl]hexahydro-1,3,5-triazine (V)
2-Phenyl-1-(2-vinyloxyethyl)imidazolidine (IIIa)
and N-benzylidene-N′-(2-vinyloxyethyl)ethane-1,2-
diamine (IVa). Yield of mixture IIIa/IVa 79%,
bp 151–155°C (3 mm), nD20 = 1.5398. IR spectrum, ν,
cm–1: 3290, 3116, 3062, 2932, 2881, 2832, 1.645,
1618, 1600, 1581, 1493, 1454, 1430, 1370, 1320,
1
which was isolated in 88% yield. The H NMR spec-
trum of compound V contained a singlet from the
NCH2N proton at δ 3.44 ppm, and the corresponding
carbon atom resonated in the 13C NMR spectrum at
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 4 2010

CONDENSATION OF N-(2-VINYLOXYETHYL)ETHANE-1,2-DIAMINE
497
1294, 1205, 1130, 1076, 1026, 998, 964, 817, 756,
697, 633. H NMR spectrum, δ, ppm: IIIa: 2.05 br.s
CH2NH), 66.46 (OCH2), 81.61 (NCHN), 86.21
(=CH2), 122.19 (C3, C5), 142.29 (C4), 149.57 (C2, C6),
151.05 (OCH=); IVb: 48.02 (OCH2CH2NH), 49.17
(NHCH2CH2N), 60.91 (CH2N=), 66.80 (OCH2), 86.21
(=CH2), 121.45 (C3, C5), 142.25 (C4), 149.88 (C2, C6),
151.21 (OCH=), 159.77 (CH=N). Found, %: C 65.60;
H 7.90; N 19.38. C12H17N3O. Calculated, %: C 65.73;
H 7.81; N 19.16.
1
(1H, NH), 2.48 m (2H, NCH2CH2O), 2.8, 3.1–3.4 m
3
(4H, NCH2CH2NH), 3.79 t (2H, OCH2, J = 5.7 Hz),
2
3.96 d.d (1H, cis-CH=C, J = 2.2 Hz), 4.15 d.d (1H,
2
trans-CH=C, J = 2.2 Hz), 4.16 s (1H, NCHN),
3
3
6.43 d.d (1H, OCH=, Jcis = 6.7, Jtrans = 14.3 Hz),
7.38 m (3H, m-H, p-H), 7.70 m (2H, o-H); IVa:
3
2.05 br.s (1H, NH), 2.69 t (2H, NCH2CH2O, J =
3-[1-(2-Vinyloxyethyl)imidazolidin-2-yl]pyridine
(IIIc) and N-[(E)-pyridin-3-yl-3-methylidene]-N′-(2-
vinyloxyethyl)ethane-1,2-diamine (IVc). Yield of
3
5.5 Hz), 2.95 t (2H, NCH2CH2N=C, J = 5.6 Hz),
3
3.75 t (2H, OCH2, J = 5.5 Hz), 3.77 t (2H, CH2N=C,
2
3
3J = 5.6 Hz), 3.94 d.d (1H, cis-CH=C, J = 2.1, Jcis
=
=
=
mixture IIIc/IVc 81%, bp 163–166°C (4 mm), d420
=
2
3
1.0570, nD20 = 1.5354. IR spectrum, ν, cm–1: 3260,
3100, 3065, 3015, 2910, 2860, 2800, 1645, 1620,
1610, 1590, 1570, 1555, 1445, 1400, 1345, 1290,
1275, 1170, 1105, 1050, 1000, 970, 940, 920, 885,
6.6 Hz), 4.10 d.d (1H, trans-CH=, J = 2.1, Jtrans
14.3 Hz), 6.43 d.d (1H, OCH=, Jcis = 6.6, Jtrans
3
3
14.3 Hz), 7.40 m (3H, m-H, p-H), 7.72 m (2H, o-H),
8.31 s (1H, N=CH). 13C NMR spectrum, δC, ppm: IIIa:
46.29 (NCH2CH2NH), 51.33 (OCH2CH2N), 54.82
(NCH2CH2NH), 68.49 (OCH2), 85.10 (NCHN), 87.90
(=CH2), 128.96 (Co), 129.09 (Cm), 131.99 (Cp), 141.21
(Ci), 151.91 (OCH=); IVa: 49.85 (OCH2CH2NH),
49.91 (NHCH2CH2N), 62.60 (CH2N=), 68.70 (OCH2),
88.02 (=CH2), 129.54 (Co), 129.98 (Cm), 132.07 (Cp),
141.65 (Ci), 153.11 (OCH=), 163.68 (CH=N). Found,
%: C 71.41; H 8.49; N 12.19. C13H18N2O. Calculated,
%: C 71.53; H 8.31; N 12.83.
1
780, 685, 635, 590, 520, 460. H NMR spectrum, δ,
ppm: IIIc: 1.79 br.s (1H, NH), 2.57 m (2H, NCH2-
CH2O), 2.81 m and 2.93–2.99 m (2H, NCH2CH2NH),
3.15–3.35 m (2H, NCH2CH2NH), 3.73 t (2H, OCH2,
2
3J = 5.7 Hz), 3.96 d.d (1H, cis-CH=C, J = 2.0 Hz),
2
3
4.11 d.d (1H, trans-CH=C, J = 2.0, Jtrans = 14.3 Hz),
3
4.22 s (1H, NCHN), 6.42 d.d (1H, OCH=, Jcis = 6.6,
3Jtrans = 14.2 Hz), 7.28 m (1H, 5-H), 7.83 d.t (1H, 4-H,
3J = 7.9, 4J = 0.8 Hz), 8.56 d.d (1H, 6-H, 3J = 4.7, 4J =
4
0.8 Hz), 8.71 d (1H, 2-H, J = 1.8 Hz); IVc: 1.79 br.s
4-[1-(2-Vinyloxyethyl)imidazolidin-2-yl]pyridine
(IIIb) and N-[(E)-pyridin-4-ylmethylidene]-N′-(2-
vinyloxyethyl)ethane-1,2-diamine (IVb). Yield of
(1H, NH), 2.69 t (2H, NCH2CH2O, 3J = 5.3 Hz), 2.89 t
3
(2H, NCH2CH2N=C, J = 5.4 Hz), 3.78 t (2H, OCH2,
3
3J = 5.3 Hz), 3.79 t (2H, CH2N=C, J = 5.4 Hz),
mixture IIIb/IVb 84%, bp 138–142°C (2 mm), d420
=
2
1.0609, nD20 = 1.5400. IR spectrum, ν, cm–1: 3260,
3105, 3060, 3015, 2920, 2870, 2805, 1640, 1615,
1600, 1555, 1445, 1420, 1395, 1355, 1300, 1180, 1115,
1040, 1005, 975, 950, 930, 895, 795, 725, 680, 610,
3.98 d.d (1H, cis-CH=C, J = 1.8 Hz), 4.16 d.d (1H,
2
3
trans-CH=C, J = 1.8, Jtrans = 14.3 Hz), 6.46 d.d (1H,
OCH=, 3Jcis = 6.6 Hz), 7.34 m (1H, 5-H), 8.09 d.t (1H,
4-H, 3J = 7.9, 4J = 0.8 Hz), 8.63 d.d (1H, 6-H, 3J = 4.7,
4J = 0.8 Hz), 8.36 s (1H, N=CH), 8.70 d (1H, 2-H, 4J =
1.8 Hz). 13C NMR spectrum, δC, ppm: IIIc: 44.65
(NCH2CH2NH), 51.04 (OCH2CH2N), 53.01 (NCH2-
CH2NH), 66.49 (OCH2), 80.85 (NCHN), 86.22
(=CH2), 123.13 (C5), 134.85 (C4), 135.74 (C3), 149.33
(C2), 149.43 (C6), 151.13 (OCH=); IVc: 48.10 (OCH2-
CH2NH), 49.38 (NHCH2CH2N), 61.03 (CH2N=),
66.87 (OCH2), 86.22 (=CH2), 123.19 (C5), 131.18 (C3),
134.16 (C4), 149.79 (C2), 151.06 (C6), 151.28 (OCH=),
158.88 (CH=N). Found, %: C 65.70; H 7.60; N 19.19.
C12H17N3O. Calculated, %: C 65.73; H 7.81; N 19.16.
1
530, 470. H NMR spectrum, δ, ppm: IIIb: 1.92 br.s
(1H, NH), 2.57 m (2H, NCH2CH2O), 2.8–2.95 m (2H,
NCH2CH2NH), 3.15–3.25 m (2H, NCH2CH2NH),
3
3.74 t (2H, OCH2, J = 5.6 Hz), 3.97 d.d (1H, cis-
2
3
CH=C, J = 1.8, Jcis = 6.7 Hz), 4.12 d.d (1H, trans-
CH=C, 2J = 1.8, 3Jtrans = 14.3 Hz), 4.22 s (1H, NCHN),
3
3
6.41 d.d (1H, OCH=, Jcis = 6.7, Jtrans = 14.3 Hz),
7.43 d.d (2H, 3-H, 5-H, 3J = 4.4, 4J = 1.1 Hz), 8.58 d.d
3
4
(2H, 2-H, 6-H, J = 4.4, J = 1.4 Hz); IVb: 1.92 br.s
(1H, NH), 2.69 t (2H, NCH2CH2O, 3J = 5.3 Hz), 2.88 t
3
(2H, NCH2CH2N=C, J = 5.4 Hz), 3.78 t (2H, OCH2,
3J = 5.3 Hz), 3.79 t (2H, CH2N=C, J = 5.5 Hz),
N-Cyclopentylidene-N′-(2-vinyloxyethyl)ethane-
1,2-diamine (IVd). Yield 64%, bp 112–117°C (3 mm),
nD20 = 1.4930. IR spectrum, ν, cm–1: 3295, 3090, 3020,
2925, 2850, 2800, 1665, 1620, 1605, 1420, 1390,
1285, 1240, 1160, 1100, 1035, 985, 960, 925, 880,
3
3.97 d.d (1H, cis-CH=C), 4.16 d.d (1H, trans-CH=C,
3
2J = 1.8 Hz), 6.47 d.d (1H, OCH=, Jcis = 6.8 Hz),
3
4
7.58 d.d (2H, 3-H, 5-H, J = 4.4, J = 1.1 Hz), 8.30 s
3
4
(1H, N=CH), 8.67 d.d (2H, 2-H, 6-H, J = 4.4, J =
1.3 Hz). 13C NMR spectrum, δC, ppm: IIIb: 44.17
(NCH2CH2NH), 51.30 (OCH2CH2N), 53.04 (NCH2-
1
775, 665, 590, 460. H NMR spectrum, δ, ppm: 1.57–
2.25 m (9H, CH2, NH), 2.83 m (4H, CH2NCH2), 3.21 t
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 4 2010

KUKHAREV et al.
498
3
3
3
(2H, =NCH2, J = 6.1 Hz), 3.79 t (2H, OCH2, J =
14.3 Hz); minor isomer: 0.88 (6H, CHMe2, J =
2
3
5.3 Hz), 3.97 d.d (1H, cis-CH=C, J = 1.8, Jcis
6.7 Hz), 4.17 d.d (1H, trans-CH=C, J = 1.8, Jtrans
14.3 Hz), 6.47 d.d (1H, OCH=, Jcis = 6.8, Jtrans
=
=
=
6.7 Hz), 1.80 s (3H, Me), 1.95 m (1H, CHMe2), 2.09 m
(3H, CH2CHMe2, NH), 2.88 m (4H, CH2NHCH2),
3.36 t (1H, CH2N=C, 3J = 6.0 Hz), 3.75 t (2H, OCH2),
3.94 d.d (1H, cis-CH=C), 4.14 d.d (1H, trans-HC=C),
6.44 d.d (1H, OCH=). Found, %: C 67.64; H 11.82;
N 13.15. C12H24N2O. Calculated, %: C 67.88; H 11.39;
N 13.19.
2
3
3
3
14.3 Hz). 13C NMR spectrum, δC, ppm: 24.28 (syn-
CN=CCH2CH2), 24.84 (anti-CN=CCH2CH2), 29.28
(syn-CN=CCH2), 36.36 (anti-CN=CCH2), 48.72
(OCH2CH2NH), 50.43 (NHCH2CH2N=), 53.31
(CH2N=), 67.37 (OCH2), 86.37 (=CH2), 151.72
(OCH=), 181.73 (N=C). Found, %: C 67.17; H 10.14;
N 14.21. C11H20N2O. Calculated, %: C 67.31; H 10.27;
N 14.27.
1,3,5-Tris[2-(2-vinyloxyethylamino)ethyl]hexa-
hydro-1,3,5-triazine (V). Yield 88%, bp 164–169°C
(2 mm), d420 = 1.0226, nD20 = 1.4953. IR spectrum, ν,
cm–1: 3280, 3110, 3075, 3025, 2915, 2870, 2805, 1625,
1605, 1480, 1460, 1425, 1395, 1345, 1310, 1280,
1185, 1060, 1010, 985, 950, 910, 870, 800, 685, 630,
580, 525. H NMR spectrum, δ, ppm: 1.83 br.s (1H,
NH), 2.62 t (2H, NHCH2CH2N, J = 7.1 Hz), 2.73 t
(2H, NHCH2CH2O, J = 5.6 Hz Hz), 3.01 t (2H,
NHCH2CH2N, J = 7.1 Hz), 3.44 s (2H, NCH2N),
N-Cyclohexylidene-N′-(2-vinyloxyethyl)ethane-
1,2-diamine (IVe). Yield 83%, bp 111–116°C (2 mm),
nD20 = 1.4998. IR spectrum, ν, cm–1: 3300, 3100, 3065,
3040, 2915, 2865, 2830, 2795, 1660, 1615, 1605,
1420, 1335, 1295, 1270, 1230, 1175, 1125, 1105, 1045,
1030, 975, 935, 880, 840, 780, 745, 680, 600, 585,
520, 460, 430. H NMR spectrum, δ, ppm: 1.30–
1.80 m (10H, CH2), 2.75 t (2H, OCH2CH2N, J =
6.1 Hz), 2.86 t (2H, =NCH2CH2, J = 6.9 Hz), 3.01 t
1
3
3
3
1
3
3.73 t (2H, OCH2, J = 5.6 Hz), 3.93 d.d (1H, cis-
CH=C, J = 1.8, Jcis = 6.9 Hz), 4.10 d.d (1H, trans-
3
2
3
3
2
3
CH=C, J = 1.8, Jtrans = 14.3 Hz), 6.43 d.d (1H,
3
OCH=, Jcis = 6.9, Jtrans = 14.3 Hz). 13C NMR spec-
trum, δC, ppm: 50.39 (NHCH2CH2O), 52.69 (NCH2-
CH2NH), 53.54 (NCH2CH2NH), 66.66 (OCH2), 75.32
(NCH2N), 86.34 (=CH2), 151.60 (OCH=). Found, %:
C 59.44; H 9.72; N 19.82. C21H42N6O3. Calculated, %:
C 59.12; H 9.92; N 19.70.
3
3
(2H, =NCH2, J = 6.9 Hz), 3.25 br.s (1H, NH), 3.73 t
(2H, OCH2, 3J = 6.1 Hz), 3.95 d.d (1H, cis-CH=C, 2J =
3
2
1.8, Jcis = 6.7 Hz), 4.13 d.d (1H, trans-CH=C, J =
1.8, 3Jtrans = 14.3 Hz), 6.44 d.d (1H, OCH=, 3Jcis = 6.7,
3Jtrans = 14.3 Hz). 13C NMR spectrum, δC, ppm: 25.11
(=CCH2CH2CH2), 27.45 (anti-CN=CCH2CH2), 28.35
(syn-CN=CCH2CH2), 32.81 (=CCH2), 49.39 (OCH2-
CH2NH), 49.88 (NHCH2CH2N=), 52.69 (CH2N=),
69.01 (OCH2), 87.80 (=CH2), 153.13 (OCH=), 172.92
(N=C). Found, %: C 68.47; H 10.30; N 13.20.
C12H22N2O. Calculated, %: C 68.53; H 10.54; N 13.32.
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N-(1,3-Dimethylbutylidene)-N′-(2-vinyloxyethyl)-
ethane-1,2-diamine (IVf). Yield 53%, bp 131–133°C
(8 mm), d420 = 0.8743, nD20 = 1.4635. IR spectrum, ν,
cm–1: 3210, 3110, 3070, 3035, 2945, 2915, 2860, 2820,
1645, 1605, 1445, 1350, 1305, 1270, 1230, 1180,
1125, 1060, 1005, 980, 945, 795, 740, 585, 515.
1H NMR spectrum, δ, ppm: major isomer: 0.86 (6H,
CHMe2, J = 6.6 Hz), 1.76 s (3H, Me), 1.95 m (2H,
CHMe2, NH), 1.95 m (1H, CHMe2), 2.09 m (3H,
CH2CHMe2, NH), 2.88 m (4H, CH2NHCH2), 3.31 t
3
3
3
4. Potapov, V.M.,
Stereokhimiya (Stereochemistry),
(2H, CH2N=C, J = 5.9 Hz), 3.75 t (2H, OCH2, J =
5.3 Hz), 3.94 d.d (1H, cis-CH=C, J = 2.0, Jcis
6.8 Hz), 4.14 d.d (1H, trans-HC=C, J = 2.0, Jtrans
14.3 Hz), 6.42 d.d (1H, OCH=, Jcis = 6.8, Jtrans
2
3
Moscow: Khimiya, 1988, p. 332.
5. Valter, R.E., Usp. Khim.,1982, vol. 51, p. 1374.
6. Bergman, E.D., Chem. Rev., 1953, vol. 53, p. 309.
=
=
=
2
3
3
3
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 4 2010