520 JOURNAL OF CHEMICAL RESEARCH 2015
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8
-1
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-Acetoxy-2-oxabicyclo[3.3.0]-3-octanone (2e): Oil; IR (neat, cm ):
Published online: 1 September 2015
1
1
1
1
1
5
759, 1178, 1013; H NMR: d 5.25–5.18 (m, 1H), 4.82 (d, J = 6.9 Hz,
H), 3.22–2.97 (m, 1H), 2.85 (dd, J = 18.3, 10.2 Hz, 1H), 2.3 (dd, J =
8.3, 3.0 Hz, 1H), 2.31–1.56 (m, 4H), 2.05 (s, 3H); C NMR: d 176.2,
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3
+
References
69.6, 87.4, 78.0, 36.2, 34.7, 30.7. 29.1, 20.8; MS (EI, m/z, %): 184 (M ,
2.3), 43 (100).
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4
5
V. V. Grushin, Chem. Soc. Rev., 2000, 29, 315.
M. Ochiai, Y. Takeuchi, T. Katayama, T. Sueda and K. Miyamoto, J. Am.
Chem. Soc., 2005, 127, 12244.
T. Dohi, A. Maruyama, M. Yoshimura, K. Morimoto, H. Tohma and Y.
Kita, Angew. Chem. Int. Ed., 2005, 44, 6193.
R. D. Richardson and T. Wirth, Angew. Chem. Int. Ed., 2006, 45, 4402.
A. Tanaka, K. Moriyama and H. Togo, Synlett, 2011, 1853.
M. Uyanik, D. Suzuki and T. Yasui, Angew. Chem. Int. Ed., 2011, 50, 5331.
16
-1
4
-Acetoxy-2-tetrahydrofuranone (2f): Oil; IR (neat, cm ): 1770,
1
1171, 1012; H NMR: d 5.47 (ddt, J = 6.5, 4.8, 1.5 Hz, 1H), 4.50 (dd, J
=
11.2, 4.8 Hz, 1H), 4.36 (dd, J = 11.0, 1.5 Hz, 1H), 2.94 (dd, J = 18.4,
1
3
7.0 Hz, 1H), 2.60 (dd, J = 18.2, 1.7 Hz, 1H), 2.08 (s, 3H); C NMR: d
+
6
174.5, 170.1, 72.7, 69.8, 34.3, 20.6; MS (EI, m/z, %): 144 (M , 10.8), 43
(100).
7
8
9
16
-1
4
-Acetoxy-5-ethyl-2-tetrahydrofuranone (2g): Oil; IR (neat, cm ):
1
1750, 1156, 1024; H NMR: d 5.49 (dd, J = 6.0, 5.2 Hz, 1H), 4.48 (ddd,
J = 8.4, 5.2, 4.0 Hz, 1H), 2.92 (dd, J = 18.4, 6.0 Hz, 1H), 2.58 (d, J =
8.4 Hz, 1H), 2.09 (s, 3H), 1.98–1.66 (m, 2H), 1.06 (t, J = 7.5 Hz, 3H);
10 K. V. V. Krishna Mohan, N. Narender and S. J. Kulkarni, Tetrahedron Lett.,
004, 45, 8015.
2
1
1
1
M. Uyanik, H. Okamoto and T. Yasui, Science, 2010, 328, 1376.
Z. S. Zhou and X. H. He, J. Chem. Res., 2014, 38, 630.
H. Ohta, Y. Sakata and T. Takeuchi, Chem. Lett., 1990, 19, 733.
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3
C NMR: d 174.0, 170.0, 84.2, 70.5, 36.8, 21.9, 20.6, 9.8; MS (EI, m/z,
12
3
+
%
): 172 (M , 30.5), 43 (100).
1
1
9
-1
6
-Acetoxymethyl-2-tetrahydropyranone (2h): Oil; IR (neat, cm ):
14 G. Asensio, C. Andreu, C. Boix-Bernardini, R. Mello and M. E. Gonzalez-
Nunez, Org. Lett., 1999, 1, 2125.
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1
2
1
758, 1203; H NMR: d 4.76–4.70 (m, 1H), 4.38–4.14 (m, 2H),
13
.57–2.35 (m, 2H), 2.10 (s, 3H), 1.98–1.80 (m, 4H); C NMR: d 175.8,
16
M. Tiecco, L. Testaferri, M. Tingoli and D. Bartoli,
+
70.9, 77.1, 65.8, 28.3, 25.6, 23.2, 20.4; MS (EI, m/z, %): 172 (M , 4.8),
Tetrahedron, 1990, 46, 7139.
17 H.-J. Ha, K.-N. Yoon, S.-Y. Lee, Y.-S. Park, M.-S. Lim and Y.-G. Yim, J.
Org. Chem., 1998, 63, 8062.
4
3 (100).
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0
-1
2
-Acetoxymethyltetrahydrofuran (2j): Oil; IR (neat, cm ): 1745,
1
18 M. Tiecco, L. Testaferri and M. Tingoli, Tetrahedron, 1993, 49, 5351.
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3
1
237, 1043; H NMR: d 4.14–4.02 (m, 2H), 4.00–3.90 (m, 1H),
.85–3.72 (m, 2H), 2.09 (s, 3H), 2.05–1.85 (m, 3H), 1.70–1.57 (m,
H); C NMR: d 170.8, 78.4, 71.5, 65.7, 27.5, 23.9, 20.1; MS (EI, m/z,
19
13
2
0
A. Kamal, M. N. A. Khan, K. S. Reddy, Y. V. V. Srikanth and T. Krishnaji,
Tetrahedron Lett., 2007, 48, 3813.
+
%
): 144 (M , 23.3), 43 (100).