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T. Kitamura et al.
SPECIAL TOPIC
1H NMR (300 MHz, CDCl3): δ = 0.92 (t, J = 7.2 Hz, CH3), 0.94 (t,
J = 7.2 Hz, CH3), 1.29–1.36 (m, CH2 and CH3), 1.57–1.64 (m,
CH2), 2.52 (t, J = 7.2 Hz, CH2), 2.68–2.74 (m, CH2), 4.26–4.33 (m,
CH2), 4.79 (s, 1 H, CH), 12.42 (s, OH).
13C NMR (75 MHz, CDCl3): δ = 13.66, 13.67, 13.87, 14.07, 21.94,
22.26, 25.47, 27.81, 32.57, 38.55, 60.89, 61.87, 63.00, 96.39,
165.01, 169.50, 175.87, 198.96.
13C NMR (75 MHz, CDCl3): δ = 40.74, 64.46, 67.62, 125.05,
125.45, 127.89, 129.65, 139.80, 139.83.
1,2-Dichloro-1,2,3,4-tetrahydronaphthalene (11a)15
Yield: 177 mg (88%); colorless oil.
1H NMR (300 MHz, CDCl3): δ = 2.09–2.14 (m, 1 H, CH), 2.59–
2.70 (m, 1 H, CH), 2.80–2.88 (m, 1 H, CH), 3.08–3.19 (m, 1 H, CH),
4.61–4.65 (m, 1 H, CH), 5.22 (d, J = 3.0 Hz, 1 H, CH), 7.11–7.35
(m, 4 H, ArH).
2-Chloro-1-phenylbutan-1,3-dione (4a)12
Yield: 138 mg (70%); colorless oil.
1H NMR spectrum in CDCl3 showed that 4a contained 27% of the
13C NMR (75 MHz, CDCl3): δ = 23.85, 25.03, 59.45, 59.76, 126.64,
128.75, 129.01, 131.00, 132.36, 134.84.
enol form.
1H NMR (300 MHz, CDCl3): δ = 2.29 (s, CH3), 2.34 (s, CH3), 5.51
(s, CH), 7.35–7.91 (m, ArH).
References
13C NMR (75 MHz, CDCl3): δ = 25.50, 26.59, 64.14, 106.66,
127.92, 128.71, 128.91, 129.30, 131.27, 133.61, 134.41, 134.48,
180.42, 189.80, 195.08, 198.59.
(1) (a) Hudlicky, M.; Hudlicky, T. In The Chemistry of Halides,
Pseudo-Halides and Azides, Supplement D; Patai, S.;
Rappaport, Z., Eds.; Wiley: Chichester, 1983, Chap. 22.
(b) Sandler, S. R.; Karo, W. Organic Functional Group
Preparations, 2nd ed.; Academic Press: New York, 1983,
Chap. 6. (c) Larock, R. C. Comprehensive Organic
Transformations, 2nd ed.; Wiley-VCH: New York, 1999.
(2) (a) Varvoglis, A. Hypervalent Iodine in Organic Synthesis;
Academic Press: New York, 1997. (b) Zhdankin, V. V.;
Stang, P. J. Chem. Rev. 2008, 108, 5299, and references cited
therein.
(3) Lucas, H. J.; Kennedy, E. R. Org. Synth. Coll. Vol. 3; Wiley:
New York, 1955, 482-48.
(4) Kitamura, T.; Kuriki, S.; Morshed, M. H.; Hori, Y. Org. Lett.
2011, 13, 2392.
(5) (a) Zefirov, N. S.; Safronov, S. O.; Kaznacheev, A. A.;
Zhdankin, V. V. Zh. Org. Khim. 1989, 25, 1807.
(b) Salamant, W.; Hulme, C. Tetrahedron Lett. 2006, 47,
605.
2-Chloro-1,3-diphenylpropan-1,3-dione (5a)12
Yield: 235 mg (91%); white crystals; mp 86−87 °C.
1H NMR (300 MHz, CDCl3): δ = 5.30 (s, 1 H, CH), 7.11 (t, J = 7.2
Hz, 4 H, ArH), 7.33 (t, J = 7.2 Hz, 2 H, ArH), 7.71 (d, J = 7.2 Hz, 4
H, ArH).
13C NMR (75 MHz, CDCl3): δ = 62.14, 128.79, 128.97, 133.64,
134.15, 189.28.
1,2-Dichloro-1-phenylethane (6a)13
Yield: 98 mg (56%); yellow oil.
1H NMR (300 MHz, CDCl3): δ = 3.88–4.01 (m, 2 H, CH2), 4.96–
5.01 (m, 1 H, CH), 7.35–7.42 (m, 5 H, ArH).
13C NMR (75 MHz, CDCl3): δ = 48.32, 61.73, 127.37, 128.78,
129.13, 137.97.
(6) Heasley, G. E.; Bower, T. R.; Doughharty, K. W.; Easdon, J.
C.; Heasley, V. L.; Arnold, S.; Carter, T. L.; Yaeger, D. B.;
Gipe, B. T.; Shellhamer, D. F. J. Org. Chem. 1980, 45, 5150.
(7) (a) Podgoršek, A.; Jurisch, M.; Stavber, S.; Zupan, M.; Iskra,
J.; Gladysz, J. A. J. Org. Chem. 2009, 74, 3133. (b) Chen, J.-
M.; Zeng, X.-M.; Middleton, K.; Zhdankin, V. V.
Tetrahedron Lett. 2011, 52, 1952.
(8) Frantz, R.; Hintermann, L.; Perseghini, M.; Broggini, D.;
Togni, A. Org. Lett. 2003, 5, 1709.
(9) Mei, Y.; Bentley, P. A.; Du, J. Tetrahedron Lett. 2008, 49,
3802.
Ethyl 2,3-Dichloro-3-phenylpropanoate (7a)14
Yield: 180 mg (73%); colorless oil; a 46:54 mixture of stereoiso-
mers.
1H NMR (300 MHz, CDCl3): δ = 1.06 (t, J = 7.2 Hz, CH3), 1.36 (t,
J = 7.2 Hz, CH3), 4.04 (q, J = 7.2 Hz, CH2), 4.34 (q, J = 7.2 Hz,
CH2), 4.60 (d, J = 10.7 Hz, CH), 4.65 (d, J = 8.4 Hz, CH), 5.18 (d,
J = 10.7 Hz, CH), 5.28 (d, J = 8.4 Hz, CH), 7.30–7.44 (m, ArH).
13C NMR (75 MHz, CDCl3): δ = 13.65, 13.91, 58.98, 61.04, 62.37,
62.58, 62.59, 63.63, 127.78, 128.05, 128.68, 128.75, 129.38,
136.41, 136.84, 166.53, 167.39.
(10) Perrone, M. G.; Santandrea, E.; Dell’Uomo, N.; Giannessi,
F.; Milazzo, F. M.; Sciarroni, A. F.; Scilimati, A.; Tortorella,
V. Eur. J. Med. Chem. 2005, 40, 143.
(11) Takeda, A.; Amano, E.; Tsuboi, S. Bull. Chem. Soc. Jpn.
1977, 50, 2191.
(12) Roshchupkina, G. I.; Gatilov, Y. V.; Rybalova, T. V.;
Reznikov, V. A. Eur. J. Org. Chem. 2004, 1765.
(13) Iranpoor, N.; Firouzabadi, H.; Aghapour, G.; Nahid, A. Bull.
Chem. Soc. Jpn. 2004, 77, 1885.
(14) Kamigata, N.; Satoh, T.; Yoshida, M. Bull. Chem. Soc. Jpn.
1988, 61, 449.
1,2-Dichloro-1,2-diphenylethane (8a)14
Yield: 226 mg (90%) for entry 7, Table 2 and 234 mg (93%) for en-
try 8, Table 2; white crystals; mp 188–195 °C; a mixture of stereo-
isomers.
1H NMR (300 MHz, CDCl3): δ = 5.21 (s, CH), 5.23 (s, CH), 7.13-
7.21 (m, ArH), 7.34–7.44 (m, ArH).
13C NMR (75 MHz, CDCl3): δ = 65.70, 67.66, 128.01, 128.07,
128.12, 128.49, 128.60, 128.94, 137.25, 138.29.
trans-1,2-Dichloroindane (trans-10a)6
Yield: 144 mg (77%); yellow oil.
1H NMR (300 MHz, CDCl3): δ = 3.13–3.20 (m, 1 H, CH), 3.65–
3.72 (m, 1 H, CH), 4.62–4.66 (m, 1 H, CH), 5.33 (d, J = 2.7 Hz, 1
H, CH), 7.23–7.45 (m, 4 H, ArH).
(15) Adam, W.; Mock-Knoblauch, C.; Saha-Moeller, C. R.;
Herderich, M. J. Am. Chem. Soc. 2000, 122, 9685.
Synthesis 2012, 44, 1159–1162
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