S. Velusamy et al. / Tetrahedron 61 (2005) 2011–2015
2015
(CDCl ) d 13.8, 20.2, 20.4, 26.4, 63.5, 123.4, 134.1, 170.5;
IR (neat) 1741 cm . Anal. Calcd for C H O : C, 67.57;
H, 9.92. Found: C, 67.58; H, 9.94.
A. R.; Gold, V. J. Chem. Soc. 1961, 4362. (f) Vedejs, E.;
Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.;
Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286.
. For Lewis acid catalysed reactions: (a) Ganem, B.; Small,
V. R., Jr. J. Org. Chem. 1974, 39, 3728. (b) Iqbal, J.;
Srivastava, R. R. J. Org. Chem. 2001, 1992, 57. (c) Izumi, J.;
Shiina, I.; Mukaiyama, T. Chem. Lett. 1995, 141. (d) Vedejs,
E.; Daugulis, O. J. Org. Chem. 1996, 61, 5702. (e) Damen,
E. W. P.; Braamer, L.; Scheeren, H. W. Tetrahedron Lett.
1998, 39, 6081. (f) Orita, A.; Tanahashi, C.; Kakuda, A.;
Otera, J. Angew. Chem., Int. Ed. 2000, 39, 2877. (g) Orita, A.;
Tanahashi, C.; Kakuda, A.; Otera, J. J. Org. Chem. 2001, 66,
3
K1
8
14 2
6
4
9
3
1
.1.2. Propane-1,2-diacetate (3p). Colorless liquid. Yield
1
2%. H NMR (CDCl ) d 1.25 (d, 3H, JZ6.6 Hz), 2.06 (s,
3
H), 2.08 (s, 3H), 4.05 (dd, 1H, JZ6.6, 11.7 Hz), 4.17 (dd,
1
3
H, JZ3.6, 12.0 Hz), 5.08–5.18 (m, 1H); C NMR
(
(
CDCl ) d 16.4, 20.7, 21.1, 66.0, 68.2, 170.4, 170.7; IR
3
K1
neat) 1742 cm . Anal. Calcd for C H O : C, 52.49; H,
7
12 4
7
.55. Found: C, 52.50; H, 7.53.
8
926. (h) Tangestaninejad, S.; Habibi, M. H.; Mirkhani, V.;
4
4
.1.3. Benzyl phenylacetate (4d). Colorless liquid. Yield
4%. H NMR (CDCl ) d 3.6 (s, 2H), 5.1 (s, 2H), 7.2–7.4
1
Moghadam, M. Synth. Commun. 2002, 32, 1337. (i) Lee, J.-C.;
Tai, C.-A.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 851.
3
1
3
(
m, 10 H); C NMR (CDCl ) d 41.8, 67.0, 127.4, 128.5,
3
(
j) Carrigan, M. D.; Freiberg, D. A.; Smith, R. C.; Zerth, H. M.;
1
28.8, 129.6, 133.3, 134.2, 136.1, 171.5; IR (neat)
750 cm . Anal. Calcd for C H O : C, 79.62; H, 6.24.
K1
Mohan, R. S. Synthesis 2001, 2091. (k) Nakae, Y.; Kusaki, I.;
Sato, T. Synlett 2001, 1584. (l) Bartoli, G.; Bosco, M.;
Dalpozzo, R.; Marcantoni, E.; Massaccesi, M.; Sambri, L. Eur.
J. Org. Chem. 2003, 4611. (m) Kawabata, T.; Mizugaki, T.;
Ebitani, K.; Kaneda, K. Tetrahedron Lett. 2003, 44, 9205.
. Bertin, J.; Kagan, H. B.; Luche, J. L.; Setton, R. J. Am. Chem.
Soc. 1974, 96, 8113.
1
Found: C, 79.64; H, 6.25.
1
6 14 2
4
9
.1.4. Decyl trifluoroacetate (4e). Colorless liquid. Yield
1
5%. H NMR (CDCl ) d 0.9 (t, 3H, JZ7.0 Hz), 1.28–1.37
3
7
8
9
(
m, 14H), 1.73–1.76 (m, 2H), 4.3–4.4 (t, 2H, JZ7.0 Hz);
1
3
C NMR (CDCl ) d 14.3, 23.0, 25.9, 28.4, 29.8, 29.9,
2.2, 68.5, 157.2, 157.7, 158.0, 158.2, 171.9; IR (neat)
794 cm . Anal. Calcd for C H O F : C, 56.68; H, 8.32.
3
. Loupy, A.; Petit, A.; Ramdani, M.; Yvanaeff, C.; Majdoub, M.;
Labiad, B.; Villemin, A. Can. J. Chem. 1993, 71, 90.
. (a) Barrett, A. G. M.; Braddock, D. C. Chem. Commun. 1997,
3
K1
1
Found: C, 56.66; H, 8.33.
1
2 21 2 3
3
51. (b) Barrett, A. G. M.; Braddock, D. C.; Henschke, J. P.;
Walker, E. R. J. Chem. Soc., Perkin Trans. 1 1999, 873.
(c) Saravanan, P.; Singh, V. K. Tetrahedron Lett. 1999, 40,
4
4
1
6
2
1
.1.5. Decyl phenylacetate (4h). Colorless liquid. Yield
1
0%. H NMR (CDCl ) d 0.9 (t, 3H, JZ6.8 Hz), 1.3–1.5 (m,
3
2611. (d) Sharma, G. V. M.; Mahalingam, A. K.; Nagarajan,
M.; Ilangovan, A.; Radhakrishna, P. Synlett 1999, 1200.
4H), 1.5–1.7 (m, 2H), 3.6 (s, 2H), 3.9–4.2 (t, 2H, JZ
1
.8 Hz), 7.1–7.4 (m, 5H); C NMR (CDCl ) d 14.6, 23.2,
3
3
1
1
0. (a) Ishihara, K.; Ohara, S.; Yamamoto, H. Science 2000, 290,
1140. (b) Xiang, J.; Orita, A.; Otera, J. Angew. Chem., Int. Ed.
9.3, 29.4, 29.7, 29.8, 30.0, 32.3, 65.3, 127.2, 128.7, 129.4,
34.4, 171.7; IR(neat) 1751 cm . Anal. Calcd for
K1
2002, 41, 4117. (c) Xiang, J.; Orita, A.; Otera, J. Organomet.
Chem. 2002, 648, 246.
1. (a) Iqbal, J.; Srivastava, R. R. Tetrahedron Lett. 1991, 32,
C H O : C, 78.21; H, 10.21. Found: C, 78.22; H, 10.18.
18 28 2
1
663. (b) Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47,
155. (c) Iqbal, J.; Khan, M. A.; Nayyar, N. N. Tetrahedron
Acknowledgements
3
Lett. 1991, 32, 5179. (d) Nayyar, N. N.; Reddy, M. M.; Iqbal, J.
Tetrahedron Lett. 1991, 32, 6965. (e) Bhatia, B.; Reddy,
M. M.; Iqbal, J. Tetrahedron Lett. 1993, 34, 6301. (f) Bhatia,
B.; Punniyamurthy, T.; Iqbal, J. J. Org. Chem. 1993, 58, 5118.
2. (a) Velusamy, S.; Punniyamurthy, T. Tetrahedron Lett. 2004,
This work was supported by the Department of Science and
Technology (Sanction No. SR/S1/OC-092002), New Delhi
and by the Council of Scientific and Industrial Research
(
Sanction No. 01(1804)/02/EMR-II), New Delhi.
1
45, 203. (b) Velusamy, S.; Punniyamurthy, T. Tetrahedron
Lett. 2004, 45, 4917.
1
1
3. Chandra, K. L.; Saravanan, P.; Singh, R. K.; Singh, V. K.
Tetrahedron 2002, 58, 1369.
4. Hajipour, A. R.; Mazloumi, G. H. Synth. Commun. 2002, 32, 23.
References and notes
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2
3
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1
3
1
Jacqlynn, B., Eds.; The Aldrich Library of C and H FT
NMR Spectra; Aldrich Chemical: Milwauke, 1993; Vol. III.
(
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