V. Kavala, B. K. Patel
FULL PAPER
Kochhar, B. S. Bal, R. P. Deshpande, S. N. Rajadhyaksha, H.
H), 6.91 (d, J ϭ 8.7 Hz, 2 H), 7.45 (d, J ϭ 8.4, 2 H), 7.64 (s, 1 H)
ppm. 13C NMR (75 MHz, CDCl3): δ ϭ 18.4, 18.6, 33.8, 55.1, 89.5,
113.8, 127.9, 131.9, 160.4, 174.8 ppm. IR (KBr): ν˜ ϭ 2981, 2940,
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2884, 1762, 1624, 1516, 1470, 1255, 1158, 1035, 963, 834 cmϪ1
.
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123, 3671.
687.
M. Sandberg, L. K. Sydnes, Org. Lett. 2000, 2,
C16H22O5 (294.35): calcd. C 65.29, H 7.53; found C 65.39, H, 7.69.
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J. S. Yadav, B. V. S. Reddy, G. S. K. K. Reddy, Tetra-
[2d]
1,1-Diisobutyryloxy-3-phenylprop-2-ene (16c): 1H NMR (300 MHz,
CDCl3): δ ϭ 1.21 (m, 12 H), 2.56 (m, 2 H), 6.22 (dd, J ϭ 6.3,
15.9 Hz, 1 H), 6.83 (d, J ϭ 15.9 Hz, 1 H), 7.29 (m, 6 H) ppm. 13C
NMR (75 MHz, CDCl3): δ ϭ 18.2, 18.5, 18.6, 18.7, 33.7, 33.8, 35.0,
50.4, 89.5, 121.9, 127.0, 128.6, 128.7, 129.1, 135.2, 174.8 ppm. IR
(KBr): ν˜ ϭ 3032, 2976, 2935, 2879, 1757, 1470, 1245, 1205, 1158,
1096, 958 cmϪ1. C17H22O4 (290.36): calcd. C 70.32, H 7.64; found
C 69.99, H, 7.79.
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9-(Diisobutyryloxymethyl)anthracene (23c): M.p. 132Ϫ134 °C. 1H
NMR (300 MHz, CDCl3): δ ϭ 1.09 (d, J ϭ 6.9 Hz, 6 H), 1.21 (d,
J ϭ 6.9, 6 H), 2.61(m, 2 H), 7.47 (t, J ϭ 7.2 Hz, 2 H), 7.58 (t, J ϭ
8.4 Hz, 2 H), 8.0 (d, J ϭ 8.4 Hz, 2 H), 8.51 (s, 1 H), 8.72 (d, J ϭ
9 Hz, 2 H), 9.20 (s, 1 H) ppm. 13C NMR (75 MHz, CDCl3): δ ϭ
?18.4, 18.7, 33.9, 49.9, 87.6, 124.7, 125.0, 125.6, 126.5, 128.9, 129.9,
130.4, 131.4, 175.0 ppm. IR (KBr):2976, 2930, 2879, 1757, 1470,
1388, 1250, 1194, 1158, 1050, 974, 738 cmϪ1. MS (FAB): [Mϩ]
calcd. for C23H24O4 364.45; found 364. C23H24O4 (364.45): calcd.
C 75.80, H 6.64; found C 76.01, H, 6.71.
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A. Ghribi, A.
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3517.
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1,1-Dipivaloyloxy-1-(4-methoxyphenyl)methane (11d): 1H NMR
(400 MHz, CDCl3): δ ϭ 1.21 (s, 18 H), 3.81 (s, 3 H), 6.90 (d, J ϭ
8.8 Hz, 2 H), 7.41 (d, J ϭ 8.8 Hz, 2 H), 7.60 (s, 1 H) ppm. 13C
NMR (100 MHz, CDCl3): δ ϭ 27.0, 38.9, 55.3, 89.5, 113.7, 127.7,
128.0, 160.1, 176.0 ppm. IR (KBr): ν˜ ϭ 2981, 2935, 2873,1757,
1481, 1281, 1168, 1112, 968 cmϪ1. MS (FAB): [Mϩ] calcd. for
C18H26O5 322.40; found 322. C18H26O5 (322.40): calcd. C 67.06, H
8.13; found C 66.88, H, 8.28.
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355.
1,1-Dibenzoyloxy-3-phenylprop-2-ene (16e): M.p. 145Ϫ147 °C. 1H
NMR (300 MHz, CDCl3): δ ϭ 6.49 (dd, J ϭ 6.3, 16.2 Hz, 1 H),
7.05 (d, J ϭ 16.2, 1 H), 7.32Ϫ7.55 (m, 11 H), 7.85 (d, J ϭ 6.3 Hz,
1 H), 8.11 (d, J ϭ 7.5 Hz, 4 H) ppm. 13C NMR (75 MHz, CDCl3):
δ ϭ 90.7, 121.9, 127.1, 128.4, 128.7, 128.8, 129.2, 130.0, 133.5,
135.8, 164.4 ppm. IR (KBr): ν˜ ϭ 3073, 3027, 2981, 1737, 1603,
1455, 1281, 1250, 1148, 1061, 958, 702 cmϪ1. MS (FAB) [Mϩ]
calcd. for C23H18O4 358.40, found 358.0. C23H18O4 (358.40): calcd.
C 77.08, H 5.06; found C 76.88, H, 5.28.
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J. K. Michie, J. A. Miller, Synthesis 1981, 824.
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[11]
[12]
[13]
[14]
9-(Dibenzoyloxymethyl)anthracene (23e): M.p. 171.5Ϫ173 °C. 1H
NMR (300 MHz, CDCl3): δ ϭ 7.32 (m, 4 H), 7.46 (m, 4 H), 7.67
(t, J ϭ 8.4 Hz, 2 H), 7.98 (d, J ϭ 8.7 Hz, 2 H), 8.06 (d, J ϭ 7.8 Hz,
3 H), 8.48 (s, 1 H), 9.02 (d, 2 H), 9.82 (s, 1 H) ppm. 13C NMR
(75 MHz, CDCl3): δ ϭ 88.3, 124.6, 125.1, 125.4, 126.9, 128.4,
129.1, 130.0, 130.6, 131.4, 133.5, 164.5 ppm. IR (KBr): ν˜ ϭ 3063,
3007, 1747, 1726, 1286, 1250, 1081, 1061, 963 cmϪ1. MS (FAB)
[Mϩ] calcd. for C29H20O4 432.48; found 432.0. C29H20O4 (432.48):
calcd. C 80.54, H 4.66; found C 80.42, H, 4.78.
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B. Karimi, R. J. Ebrahimiam, H. Seradj, Synth. Commum.
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N. Sumida, K. Nishioka, T. Sato, Synlett 2001, 1921.
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Acknowledgments
A. J. Fry, A. K. Rho, L. R. Sherman, C. S. Sherwin, J.
Org. Chem. 1991, 56, 3283.
B. K. P. acknowledges the support of this research from DST New
Delhi SP/S1/G-28/98 and CSIR 01(1688)/00/EMR-II and V. K.
acknowledges financial support from his institute. Thanks are due
to CIF IIT Guwahati, RSIC, Lucknow, and IIT, Kanpur, for pro-
viding the NMR spectra maximize enterprising.
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© 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Org. Chem. 2005, 441Ϫ451