298 JOURNAL OF CHEMICAL RESEARCH 2016
1
3
13
2
1
.10 (s, 3H), 2.06 (s, 3H); C NMR (CDCl , 75.5 MHz): δ 170.64,
2.07 (s, 3H); C NMR (CDCl , 75.5 MHz): δ 170.49, 170.41, 70.39,
3
3
–1
70.05, 136.50, 128.64, 128.63, 126.70, 73.32, 66.09, 21.10, 20.78;
FTIR (νmax cm , neat): 3034, 2954, 1743, 1455, 1435, 1371, 1223, 1047.
,2-Diacetoxy-3-phenoxypropane (2b): H NMR (CDCl , 300
62.36, 42.10, 20.86, 20.79; FTIR (νmax cm , neat): 2963, 1744, 1436,
1371, 1221, 1046.
–1
1
1
3
MHz): δ 7.32–7.25 (m, 2H), 6.99–6.89 (m, 3H), 5.41–5.34 (m, 1H), 4.43
The authors gratefully acknowledge the financial support of
this work by the Research Council of Urmia University.
(
2
dd, J = 3.9, 12 Hz, 1H), 4.29 (dd, J = 6, 12 Hz, 1H), 4.11 (d, J = 5.1 Hz,
H), 2.09 (s, 3H), 2.06 (s, 3H); C NMR (CDCl , 75.5 MHz): δ 170.57,
13
3
1
2
1
70.26, 158.27, 129.53, 121.36, 114.59, 69.76, 65.96, 62.54, 20.92,
0.70; FTIR (νmax cm , neat): 3041, 2957, 1746, 1600, 1588, 1497, 1371,
Paper 1503807 doi: 10.3184/174751916X14604770409296
Published online: 19 April 2016
–1
228, 1050.
1
1,2-Diacetoxycyclohexane (3b): H NMR (CDCl , 300 MHz):
3
δ 4.79–4.5 (m, 2H), 1.97–1.93 (m, 2H), 1.94 (s, 3H), 1.93 (s, 3H),
References
13
1
.69–1.62 (m, 2H), 1.36–1.16 (m, 4H); C NMR (CDCl , 75.5 MHz):
3
1
A.K. Yudin, Aziridines and epoxides in organic synthesis. Wiley,
δ 170.37, 170.22, 73.49, 30.16, 29.94, 23.25, 23.11, 21.17, 21.14; FTIR
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–
1
(
νmax cm , neat): 2942, 2866, 1739, 1452, 1368, 1251, 1042.
th
2
P.G.M. Wuts and T.W. Greene, Protective groups in organic synthesis, 4
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1
1
,2-Diacetoxy-3-allyloxypropane (4b): H NMR (CDCl , 300 MHz):
3
δ 5.92–5.76 (m, 1H), 5.27 (dd, J = 1.5, 17.4 Hz, 2H), 5.21 (dd, J = 3,
3
4
5
6
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1
3
(
1
s, 3H), 2.03 (s, 3H); C NMR (CDCl , 75.5 MHz): δ 170.58, 170.26,
3
–1
34.13, 117.33, 72.19, 70.21, 68.07, 62.80, 20.94, 20.67; FTIR (νmax cm ,
neat): 2957, 2868, 1743, 1433, 1372, 1225, 1092, 1048.
7
8
1
1
,2-Diacetoxy-3-isopropoxypropane (5b): H NMR (CDCl , 300
3
MHz): δ 5.15–4.96 (m, 1H), 4.28 (dd, J 3.6, 12 Hz, 1H), 4.12 (dd, J 3,
9
C.S. Swindell and B.P. Patel, J. Org. Chem., 1990, 55, 3.
1
2 Hz, 1H), 3.58–3.40 (m, 3H), 2.05 (s, 3H), 2.04 (s, 3H), 1.09 (d, J = 6
13
10 N. Azizi, B. Mirmashhori and M.R. Saidi, Catal. Commun., 2007, 8, 2198.
Hz, 6H); C NMR (CDCl , 75.5 MHz): δ 170.68, 170.34, 72.32, 70.59,
6
3
1
12
1
1
M. Abdur Rahman and B. Fraser-Reid, J. Am. Chem. Soc., 1985, 107, 5576.
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3 S. Ali and R. Bittman, J. Org. Chem., 1988, 53, 5547.
–1
6.12, 63.00, 21.91, 21.84, 21.00, 20.74; FTIR (νmax cm , neat): 2918,
2
849, 1743, 1463, 1371, 1229, 1118, 1047.
1
1,2-Diacetoxyhexane (6b): H NMR (300 MHz, CDCl ): δ 5.12–5.16
14 R.M. Evans, J.B. Fraser and L.N. Owen, J. Chem. Soc., 1949, 248.
15 R. Dalpozzo, A. De Nino, M. Nardi, B. Russo and A. Procopio, ARKIVOC,
2006, vi, 67.
3
(
3
m, 1H), 4.10–4.33 (m, 2H), 3.35–3.42 (m, 2H), 2.06 (s, 3H), 2.04 (s,
H), 1.53–1.55 (m, 2H), 1.48–1.51 (m, 2H), 0.85 (t, 3H); C NMR (75
13
16
M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, V.
Mirkhani, L. Shariati, M. Babaghanbari and M. Zarea, J. Iran. Chem. Soc.,
MHz, CDCl ): δ 170.6, 170.3, 70.2, 68.79, 62.9, 31.5, 20.9, 20.7, 19.2,
3
–1
1
1
3.8; FTIR (νmax cm , neat): 2960, 2873, 1746, 1459, 1372, 1225, 1120,
049, 961, 896, 843.
,2-Diacetoxy-3-butoxypropane (7b): H NMR (CDCl , 300 MHz):
2
009, 6, 789.
1
1
3
Sulfur Silicon Relat. Elem., 2016. doi: 10.1080/10426507.2015.1135439.
[Epub ahead of print].
δ 5.20–5.12 (m, 1H), 4.31 (dd, J = 3.7, 11.9 Hz, 1H), 4.13 (dd, J = 6.3, 12
Hz, 1H), 3.52 (d, J = 5.4 Hz, 2H), 3.47–3.35 (m, 2H), 2.06 (s, 3H), 2.04
1
9
B. Zeynizadeh and L. Sadighnia, Synth. Commun., 2011, 41, 637.
(
s, 3H), 1.58–1.45 (m, 2H), 1.40–1.26 (m, 2H), 0.88 (t, J = 7.3 Hz, 3H);
1
3
20 M. Gilanizadeh and B. Zeynizadeh, Curr. Chem. Lett., 2015, 4, 153.
21
C NMR (CDCl , 75.5 MHz): δ 170.73, 170.39, 71.43, 70.32, 68.83,
3
M. Gilanizadeh and B. Zeynizadeh, Iran. J. Chem. Chem. Eng., 2016, 35,
25.
J. Detry, T. Rosenbaum, S. Lütz, D. Hahn, K.E. Jaeger, M. Müller and T.
Eggert, Appl. Microbiol. Biotechnol., 2006, 72, 1107.
–1
6
2.98, 31.56, 21.05, 20.78, 19.18, 13.85; FTIR (νmax cm , neat): 2959,
2
935, 2871, 1743, 1465, 1378, 1238, 1109.
2
2
1
1,2-Diacetoxy-3-chloropropane (8b): H NMR (CDCl , 300 MHz):
3
δ 5.25–5.13 (m, 1H), 4.37–4.1 (m, 2H), 3.75–3.55 (m, 2H), 2.09 (s, 3H),
23 Aldrich catalogue of fine chemicals, 2013–2014.