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Volumn 37, Issue 7, 2008, Pages 696-697

Dynamic behavior of cyclic hemiacetals of 2-hydroxy-2-(2-hydroxyphenyl)-1, 3-indandione derivatives

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EID: 49149088315 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2008.696 Document Type: Article

Times cited : (6)

References (11)

1
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- J.-P. Poupelin, G.-S. Ruf, J.-C. Perche, J.-C. Roussey, B. Laude, G. Narcisse, F. B.-Logeais, F. Hubert, Eur. J. Med. Chem. 1980, 15, 253.
- a) J.-P. Poupelin, G.-S. Ruf, J.-C. Perche, J.-C. Roussey, B. Laude, G. Narcisse, F. B.-Logeais, F. Hubert, Eur. J. Med. Chem. 1980, 15, 253.

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- b) J.-P. Poupelin, G.-S. Ruf, J.-C. Perche, R. Lacroix, G. U-Ernouf, G. Narisse, F. Hubert, Eur. J. Med. Chem. 1979, 14, 171.
- (1979) Eur. J. Med. Chem , vol.14 , pp. 171
- Poupelin, J.-P.¹ Ruf, G.-S.² Perche, J.-C.³ Lacroix, R.⁴ U-Ernouf, G.⁵ Narisse, G.⁶ Hubert, F.⁷

3
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- c) H. N. Song, H. J. Lee, H. R. Kim, E. K. Ryu, J. N. Kim, Synth. Commun. 1999, 29, 3303.
- (1999) Synth. Commun , vol.29 , pp. 3303
- Song, H.N.¹ Lee, H.J.² Kim, H.R.³ Ryu, E.K.⁴ Kim, J.N.⁵

4
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- d) H. N. Song, M. R. Seong, H. J. Lee, J. N. Kim, Synth. Commun. 1999, 29, 2759.
- (1999) Synth. Commun , vol.29 , pp. 2759
- Song, H.N.¹ Seong, M.R.² Lee, H.J.³ Kim, J.N.⁴

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- e) J. L. Bullington, J. H. Dodd, J. Org. Chem. 1993, 58, 4833.
- (1993) J. Org. Chem , vol.58 , pp. 4833
- Bullington, J.L.¹ Dodd, J.H.²

6
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- f) S. Das, R. Frohlich, A. A. Pramanik, Org. Lett. 2006, 8, 4263.
- (2006) Org. Lett , vol.8 , pp. 4263
- Das, S.¹ Frohlich, R.² Pramanik, A.A.³

7
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- g) J. E. Na, K. Y. Lee, J. Seo, J. N. Kim, Tetrahedron Lett. 2005, 46, 4505.
- (2005) Tetrahedron Lett , vol.46 , pp. 4505
- Na, J.E.¹ Lee, K.Y.² Seo, J.³ Kim, J.N.⁴

8
- 49149096909
- Crystal data of 1: C15H10O4, triclinic, space group P1̄(#2, a, 7.7910(2, b, 9.0677(2, c, 9.1110(3) Å, α, 70.857(3)°, β, 84.833(4)°, γ, 81.713(3)°, Z, 2, V, 601.09(3) Å3, Dcalc, 1.405 g/cm3, R1, I > 3.00σ(1, 0.044, wR2 (I > 3.00σI, 0.065. CCDC 679076
- 2 (I > 3.00σ(I)) 0.065. CCDC 679076.

9
- 49149086640
- This value is a rough estimation, because the coalescence method based on the interconversion between two equivalent sites is applicable to two signals without spin-coupling. The OH signals shown in Figure 3 cannot be used for estimation of ΔG‡ because the frozen spectrum is not available at -40 °C owing to proton-exchangeability. 4 For the ring-closed form of 2: 1H NMR (500 MHz, CDCl3) δ 6.92 (d, J, 9 Hz, 1H, 7.62 (t, J, 9 Hz, 1H, 7.83 (d, J, 9 Hz, 1H, 7.84 (t, J, 9 Hz, 1H, 7.96 (d, J, 9 Hz, 1H, 8.24 (dd, J, 9 Hz, 2 Hz, 1H, 8.46 (d, J, 2 Hz, 1H, For the ring-opened form of 2: 1HNMR (500 MHz, CDCl3) δ 7.07 (d, J, 9 Hz, 1H, 7.95 (d, J, 3 Hz, 1H, 7.96 and 8.08 (AA′BB′, 4H, 8.16 dd, J, 9 Hz, 3 Hz, 1H
- 3) δ 7.07 (d, J = 9 Hz, 1H), 7.95 (d, J = 3 Hz, 1H), 7.96 and 8.08 (AA′BB′, 4H), 8.16 (dd, J = 9 Hz, 3 Hz, 1H).

10
- 49149097932
- The reactions of ninhydrin with phenols such as 3-tert-butyl- phenol, 4-tert-butylphenol, 3-isopropylphenol, 5-methyl-resorcinol, and 4-phenylphenol were carried out and their hemiacetal products showed no dynamic behavior.
- The reactions of ninhydrin with phenols such as 3-tert-butyl- phenol, 4-tert-butylphenol, 3-isopropylphenol, 5-methyl-resorcinol, and 4-phenylphenol were carried out and their hemiacetal products showed no dynamic behavior.

11
- 49149094632
- 6) δ 6.60 (d, J = 8 Hz, 1H), 6.92 (t, J = 8 Hz, 1H), 7.10 (s, 1H, OH), 7.15 (t, J = 8 Hz, 1H), 7.64 (d, J = 8 Hz, 1H), 8.0-8.03 (broad s, 4H).
- 6) δ 6.60 (d, J = 8 Hz, 1H), 6.92 (t, J = 8 Hz, 1H), 7.10 (s, 1H, OH), 7.15 (t, J = 8 Hz, 1H), 7.64 (d, J = 8 Hz, 1H), 8.0-8.03 (broad s, 4H).

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