REGIOSELECTIVE RING OPENING IN EPOXIDES
1823
1
3
250 (OH), 2980 (CH ), 2830 (C–N), 1058 (C–O). H
REFERENCES
3
NMR spectrum (D O), δ, ppm: 1.35 s (3H, CH ), 2.3
2
3
m (2H, NCH ), 2.7 m (OH), 3.4 t (OCH), 3.8 s (2H,
1. Chao-Jun, L., Chem. Rev., 2005, vol. 105, p. 3095.
2
Bn), 7.30 (H, p-C H ), 7.343 m (2H, m-C H ), 7.36 m
2. Evans, G., Gibbs, T.J.K., Zenkins, R.L., Cales, S.J.,
Hursthouse, M.B., Platts, A.J., and Tomkinson, N.C.O.,
Angew. Chem., Int. Ed., 2008, vol. 47, p. 2820.
6
5
6
5
1
3
(
(
2H, o-C H ). C NMR spectrum (D O), δ , ppm: 22.2
6 5 2 C
1
3
2
C ), 53.3 m (C ), 56.6 m (C ), 65.5 (PhCH ), 126, 127,
2
1
40 (Carom). Found, %: C 72.67; H 9.15, N 8.54.
3. Kas’yan, L.I., Kas’yan, A.O., Okovityi, S.I., and Tara-
bara, I.N., Atsyklicheskie epoksidnye soedineniya. Reak-
tsionnaya sposobnost’ (Acyclic Epoxy Compounds: Re-
activity), Dnepropetrovsk: Dnepropetrovsk. Univ., 2003.
C H NO. Calculated, %: C 72.75; H 9.04, N 8.48.
1
0
14
Bis-1,3-(N,N-diethylamino)propan-2-ol (Va). This
compound was prepared from 17.7 g of diethylamine
Ia and 4.5 g of epichlorohydrin III. Yield 9.1 g (93%),
bp 122°C (10 mm Hg), nD 1.4571, d 0.9101
4
. Malinovskii, M.S., Okisi olefinov i ikh proizvodnye
Olefine Oxides and Their Derivatives), Moscow: Gos.
Khim. Inst., 1961.
(
2
0
20
4
2
D
0
{
reported data bp 64°C (0.4 mm Hg), n 1.4447 [25];
2
D
0
5. Kas’yan, L.I., Prid’ma, S.A., Turov, A.V., Pal’chikov, V.A.,
Kasyan, A.O., and Karat, L.D., Zh. Org. Khim., 2009,
vol. 45, no. 4, p. 520.
bp 110–112°C (10 mm Hg), n 1.4538 [27]}. IR
spectrum, ν, cm : 3415 (OH), 2940 (CH ), 2805 (C–N),
1
–1
3
1
115 (C–O). H NMR spectrum (D O), δ, ppm: 0.95 t
2
6. Chini, M., Crotti, P., and Macchia, F., Tetrahedron
Lett., 1990, vol. 31, no. 32, p. 4661.
(
(
(
12H, 4CH ), 2.34–2.52 m (12H, 6NCH ), 2.7 br.s
OH), 3.35 t (OCH) {reported data H NMR spectrum
CDCl ), δ, ppm: 0.92 t (12H, 4CH ), 2.34 m (4H,
3
2
1
7
. Cherbulies, E., Yazgi, A., and Rabinowitz, J., Helv.
Chim. Acta, 1961, vol. 144, no. 4, p. 1164.
3
3
CH CH), 2.48 d.t (8H, 4NCH ), 3.63 m (CH), 4.28 m
2
2
1
3
8. Hanumatharao, P., Sambosivarao, S.V., Soni, L.K.,
Gupta, A.K., and Kaskhelikar, S.C., Bioorg. Med.
Chem. Lett., 2005, vol. 15, p. 3167.
(1H, OH) [26]}. C NMR spectrum (CDCl ), δ , ppm:
3 P
3
2
1
0 (CH ), 47.1 m (C ), 57.05 m (NCH ), 66.49 (C ).
3 2
Found, %: C 65.42; H 12.97; N 13.93. C H N O.
Calculated, %: C 65.37; H 12.86; N 13.85.
1
1
26
2
9
. Shearer, B.G., Chao, E.Y., and Deaton, D.N., Bioorg.
Med. Chem. Lett., 2007, vol. 17, p. 4670.
Bis-1,3-piperidinoprpan-2-ol (Vb). This com-
pound was prepared from 25.5 g of piperidine Ia and
1
0. Merkis, A.I., Novikene, L.L., Daukshas, V.K., Sha-
ltite, Z.A., Milyuvene, L.I., and Gavelene, B.A., Zh.
Prikl. Khim., 2003, vol. 76, no. 1, p. 166.
5
1
{
.5 g of epichlorohydrin III. Yield 12 g (90%), bp
2
0
20
35–136°C (3 mm Hg), nD 1.4955, d4 1.1137
1
1
1
1
1
1
1. Huskens, J. and Reetz, M.T., Eur. J. Org. Chem., 1999,
2
D
0
reported data: bp 147–148°C (5 mm Hg), n 1.4919
vol. 8, p. 1775.
–
1
[27]}. IR spectrum, ν, cm : 3410 (OH), 2980 (CH ),
3
2. Azizi, N. and Saidi, M.R., Org. Lett., 2005, vol. 7,
1
2
800 (C–N), 1125 (C–O). H NMR spectrum (CDCl ),
3
no. 17, p. 3649.
δ, ppm: 1.28–1.53 m (12H, CH N , NCH ), 2.18 br.s
2
pip
2al
3. Fernandez-Rodriguez, M.A., Shen, Q., and Hartwig, Z.F.,
1
3
(
OH), 3.75 sept (OCH). C NMR spectrum (CDCl ),
3
J. Am. Chem. Soc., 2006, vol. 128, p. 2180.
1
3
2
δ , ppm: 24.5 (C ), 26.6 m (C ), 54.4 (CH N), 63.33
C
4. Zhu, D., Xu, L., Wu, F., and Wan, B., Tetrahedron
Lett., 2006, vol. 47, p. 5781.
2
(
N-CH ), 64.44 (C ). Found, %: C 66.13; H 11.62; N
2
1
1
2.05. C H N O. Calculated, %: C 69.03, H 11.49, N
13 26 2
5. Paut, L., Sen, T.K., and Panniyamurthy, T., Angew,
Chem. Int. Ed., 2007, vol. 46, p. 20046
2.38.
Bis-1,3-morpholinopropan-2-ol (Va). This com-
pound was prepared from 25 g of morpholine Ic and
6. Placzek, A.T., Donelson, J.L., Trivedi, R., Gibbs, R.A.,
and de Suriya, K., Tetrahedron Lett., 2005, vol. 46,
no. 52, p. 9029.
5
1
1
.4 g of epichlorohydrin III. Yield 11.6 g (87%), bp
2
0
42–144°C (2 mm Hg), n 1.4358 {reported data
D
1
7. Kleiner, Ch.M. and Schreiner, P.R., Chem. Commun.,
2
D
0
20
49–153°C (5 mm Hg), n 1.4930 [22]}, d4 0.9818.
2006, no. 41, p. 4315.
–
1
IR spectrum, ν, cm : 3422 (OH), 2940 (CH ), 2805
3
1
1
8. Griot, F., Tetrahedron, 1963, vol. 19, p. 1661.
1
(
C–N), 1110 (C–O). H NMR spectrum (CDCl ), δ,
3
9. Chapman, N.B. and Triggle, D.J., J. Chem. Soc., 1963,
ppm: 2.3 m (4H, NCH ), 2.5 m (8H, NCH ), 2.7 br.s
2
2cycl
1
3
p. 1385.
(
OH), 2.9 m (4H, 2OCH2cycl), 3.4 t (OCH). C NMR
spectrum (CDCl ), δ , ppm: 53 (C ,C ), 62 m
CH Ncycl), 63 (OCH2cycl), 66 (C ). Found, %: C 56.30;
1
3
2
0. Potekhin, A.A. and Safonov, A.O., Zh. Org. Khim.,
3
C
2
1981, vol. 17, no. 2, p. 379.
(
2
H 9.38; N 12.29. C H N O . Calculated, %: C 57.42;
21. Geartner, V.R., J. Org. Chem., 1968, vol. 33, no. 2,
1
1
32
2
3
p. 523.
H 9.56; N 12.17.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 80 No. 9 2010