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N. Zanatta et al. / Journal of Fluorine Chemistry 107 (2001) 149±154
Table 4
1H- and 13C-NMR spectral data of compounds 5a±d
Compound
1H-NMR, dppm (multiplicity, no. of protons, JHz, assignment)a 13C-NMR, dppm, JCF (Hz)b
3.54±3.60 (m, 1H, c, H-3), 5.34 (d, 1H, J43 5.6, H-4), 4.00 (t, 2H, J56 7.0, H-5), 1.90±2.10 (m, 2H, c, H-6), 3.32 (s, 3H, H-7)
5a
1
2
115.5 (q, JCF 290:4, CF3), 190.2 (q, JCF 34:9, C2), 52.8 (C3), 102.8 (C4), 66.8 (C5), 23.3 (C6), 55.0 (C7)
1
2
5a0: 115.4 (q, JCF 289:9, CF3), 186.7 (q, JCF 35:5, C2), 51.9 (C3), 102.7 (C4), 66.3 (C5), 23.0 (C6), 54.9 (C7)
3.52±3.60 (m, 1H, c, H-3), 5.48 (d, 1H, J43 5.6, H-4), 3.99 (t, 2H, J56 8.2, H-5), 2.00±2.15 (m, 2H, c, H-6), 3.69 (m, 2H, c, H-7),
1.22 (m, 3H, c, H-8)
5b
5c
1
2
115.4 (q, JCF 291:6, CF3), 190.6 (q, JCF 35:5, C2), 50.1 (C3), 101.4 (C4), 66.1 (C5), 26.6 (C6), 62.0 (C7), 14.7 (C8)
1
5b0: 116.4 (q, JCF 289:7, CF3), d (C2), 51.8 (C3), 102.0 (C4), 65.5 (C5), 27.0 (C6), 62.5 (C7), 15.6 (C8)
3.52±3.64 (m, 1H, c, H-3), 5.10±5.40 (m, 1H, c, H-4), 3.90±4.10 (m, 2H, c, H-5), 1.90±2.40 (m, 2H, c, H-6), 3.90±4.10 (m, 2H, c, H-7),
5.80±6.10 (m, 1H, c, H-8), 5.10±5.40 (m, 1H, c, H-9, H-90)
2
115.6 (q,1JCF 291:6, CF3), 190.6 (q, JCF 35:7, C2), 51.0 (C3), 100.8 (C4), 67.1 (C5), 21.5 (C6), 63.8 (C7), 137.1 (C8), 115.2 (C9)
1
2
5c0: 115.4 (q, JCF 292:4, CF3), 186.8 (q, JCF 35:2, C2), 52.9 (C3), 100.8 (C4), 66.4 (C5), 23.4 (C6), 64.5 (C7), 134.8 (C8), 114.3
(C9)
5d
3.56±3.60 (m, 1H, c, H-3), 5.40±5.70 (m, 1H, c, H-4), 3.80±4.10 (m, 2H, c, H-5), 1.90±2.30 (m, 2H, c, H-6), 4.10±4.40 (m, 2H, c, H-7),
2.40±2.50 (m, 1H, c, H-9)
1
2
123.2 (q, JCF 288:3, CF3), 189.5 (q, JCF 35:3, C2), 52.6 (C3), 99.6 (C4), 66.6 (C5), 22.9 (C6), 54.4 (C7), 78.1 (C8), 74.8 (C9)
5d0: 122.8 (q, 1JCF 287:7 (CF3), 186.6 (q, 2JCF 35:7, C2), 51.7 (C3), 99.5 (C4), 66.1 (C5), 23.2 (C6), 54.0 (C7), 78.2 (C8), 74.4 (C9)
a The NMR spectral data were obtained from the mixture of compounds 5 and 6.
b Signals of the two stereoisomers obtained; c Multiplicity and coupling constants are difficult to obtain because the signals of compound 5 are totally or
partially superimposed with the signal of the corresponding nuclei of compound 6; d Signal was not observed due to the low signal/noise ratio of the minor
isomer.
Table 5
1H- and 13C-NMR spectral data of compounds 6a±d
Compound
1H-NMR, dppm (multiplicity, no. of protons, JHz, assignment)a 13C-NMR, dppm, JCF (Hz)b
6a
2.50±2.67 (m, 1H, c, H-3), 5.14 (d, 1H, J43 4.4, H-4), 4.08 (t, 2H, J56 7.0, H-5), 2.10±2.23 (m, 2H, c, H-6), 3.43 (s, 3H, H-7), 5.56 (s,
OH)
1
2
122.8 (q, JCF 285:2, CF3), 94.2 (q, JCF 32:2, C2), 45.5 (C3), 104.2 (C4), 67.0 (C5), 27.0 (C6), 54.3 (C7)
1
2
6a0: 122.9 (q, JCF 288:5, CF3), 96.0 (q, JCF 30:4, C2), 46.7 (C3), 105.1 (C4), 67.3 (C5), 26.8 (C6), 54.3 (C7)
2.50±2.70 (m, 2H, c, H-3), 5.26 (d, 1H, J43 4.2, H-4), 4.23 (t, 2H, J56 6.20, H-6), 2.00±2.15 (m, 2H, c, H-6), 3.69 (m, 2H, c, H-7), 1.22
(t, 3H, J87 7.0, c, H-8), 5.20 (s, OH)
6b
6c
6d
1
2
122.9 (q, JCF 287:0, CF3), 93.6 (q, JCF 32:1, C2), 45.5 (C3), 102.7 (C4), 66.8 (C5), 32.6 (C6), 63.0 (C7), 14.6 (C8)
1
2
6b0: 123.3 (q, JCF 287:8, CF3), 93.2 (q, JCF 31:3, C2), 46.6 (C3), 103.7 (C4), 66.6 (C5), 30.8 (C6), 63.3 (C7), 14.3 (C8)
2.50-2.60 (m, 1H, H-3), 5.10±5.40 (m, 1H, H-4), 3.90±4.10 (m, 2H, H-5), 1.90±2.40 (m, 2H, H-6), 3.90±4.10 (m, 2H, H-7), 5.80±6.10 (m,
1H, H-8), 5.10±5.40 (m, 1H, H-9, H-90), 5.05 (s, OH)
1
116.5 (q, JCF 289:8, CF3), 93.8 (q, JCF 32.2, C2), 45.5 (C3), 102.4 (C4), 67.9 (C5), 26.8 (C6), 62.1 (C7), 133.3 (C8), 117.9 (C9)
1
6c0: 117.1 (q, JCF 285:9, CF3), d (C2), 46.5 (C3), 103.4 (C4), 68.4 (C5), 27.1 (C6), 61.7 (C7), 133.7 (C8), 117.2 (C9)
2.50±2.70 (m, 1H, c, H-3), 5.40±5.70 (m, 1H, c, H-4), 3.80±4.10 (m, 2H, c, H-5), 1.90±2.30 (m, 2H, c, H-6), 4.10±4.40 (m, 2H, c, H-7),
2.40±2.50 (m, 1H, c, H-9), 5.10 (s, OH)
1
2
115.3 (q, JCF 292:2, CF3), 93.5 (q, JCF 32:2, C2), 45.8 (C3), 101.7 (C4), 67.2 (C5), 26.9 (C6), 50.3 (C7), 81.0 (C8), 73.6 (C9)
6d0: 117.0 (q, 1JCF 280:7, CF3), 96.3 (q, 2JCF 31:2, C2), 46.4 (C3), 102.8 (C4), 67.0 (C5), 26.6 (C6), 50.1 (C7), 78.1 (C8), 74.0 (C9)
a The NMR spectral data were obtained from the mixture of compounds 5 and 6.
b Signals of the two obtained stereoisomers; c Multiplicity and coupling constants are difficult to obtain because the signals of compound 6 are totally or
partially superimposed with the signal of the corresponding nuclei of compound 5; d Signal was not observed due to the low signal/noise ratio of the minor