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T. Yamamoto et al. / Journal of Organometallic Chemistry 694 (2009) 1325–1332
4.9. Phenyl(2-naphthyl)methanol (3af) [19]
4.18. 4-Fluorophenyl(2-naphthyl)methanol (3ef) [23]
1H NMR (CDCl3): d 2.36 (brs, 1H, –OH), 5.98 (s, 1H, –OH), 7.23–
7.49 (m, 8H, -Ar), 7.76–7.88 (m, 4H, -Ar); 13C NMR (75 MHz) d 76.7,
125.0, 125.2, 126.2, 126.4, 126.9, 127.9, 128.3, 128.5, 128.8, 133.1,
133.4, 141.3, 143.8.
1H NMR (CDCl3, 300 MHz) d 2.47 (d, J = 2.1 Hz, 1H, –OH), 5.92 (d,
J = 2.1 Hz, 1H, –CHOH), 6.96–7.02 (m, 2H, -Ar), 7.31–7.37 (m, 3H,
-Ar), 7.42–7.49 (m, 2H, -Ar), 7.75–7.82 (m, 4H, -Ar); 13C NMR
(75 MHz) d 75.7, 115.2 (d, J = 21.8 Hz, –C–CF), 124.5, 124.9, 126.0,
126.2, 127.6, 127.9, 128.3 (d, J = 9.2 Hz, –C–C–CF), 128.4, 132.8,
133.1, 139.2 (d, J = 2.9 Hz, –C–C–C–CF),140.7, 162.0 (d,
J = 243.8 Hz, –CF); 19F NMR (282 MHz) d À115.0.
4.10. 4-Methylphenyl(phenyl)methanol (3ag)
1H NMR (CDCl3): d 2.21 (brs, 1H, –OH), 2.32 (s, 3H, –CH3),
5.79 (s, 1H, –CHOH), 7.11–7.38 (m, 9H, -Ar); 13C NMR (75 MHz) d
21.5, 76.4, 126.65, 126.72, 127.6, 128.6, 129.4, 137.5, 141.1,
144.1.
4.19. 4-Cyanophenyl(4-fluorophenyl)methanol (3ea) [24]
1H NMR (CDCl3, 300 MHz) d 2.49 (brs, –OH), 5.84 (s, 1H,
–CHOH), 7.00–7.05 (m, 2H, -Ar), 7.25–7.32 (m, 2H, -Ar), 7.54 (dd,
J = 30.9 and 8.1 Hzs, 4H, -Ar); 13C NMR (75 MHz) d 75.2, 111.5,
116.0 (d, J = 21.2 Hz, 2C, –C–CF),118.9, 128.6 (d, J = 8.6 Hz, 2C,
–C–C–CF), 132.5, 138.8, 148.8, 162.6 (d, J = 245.5 Hz, 1C, –CF); 19F
NMR (282 MHz) d À113.9.
4.11. 2-Methylphenyl(phenyl)methanol (3ah)
1H NMR (CDCl3): d 2.16 (brs, 1H, –OH), 2.24 (s, 3H, –CH3), 5.98
(s, 1H, –CHOH), 7.11–7.31 (m, 8H, -Ar), 7.48–7.51 (m, 1H, -Ar); 13C
NMR (75 MHz) d 19.8, 73.7, 126.3, 126.5, 127.3, 127.7, 127.8, 128.7,
130.7, 135.6, 141.6, 143.0.
4.20. 4-Cyanophenyl(2-fluorophenyl)methanol (3fa) [25]
4.12. 4-Methoxyphenyl(phenyl)methanol (3ai)
1H NMR (CDCl3, 300 MHz) d 2.68 (brs, –OH), 6.16 (s, 1H,
–CHOH), 7.00–7.60 (m, 8H, -Ar); 13C NMR (75 MHz) d 69.5, 111.5,
115.8 (d, J = 21.7 Hz, 1C, –C–CF), 119.0, 124.9 (d, J = 3.4 Hz, 1C,
–C–C–CF), 127.1, 127.8 (d, J = 3.5 Hz, 1C, –C–C–CF), 129.9, 130.2
(d, J = 16.1 Hz, 1C, –C–CF), 132.5, 148.1, 161.6 (d, J = 244.9 Hz, 1C,
–CF); 19F NMR (282 MHz) d À118.6.
1H NMR (CDCl3) d 2.34 (brs, 1H, –OH), 3.75 (s, 3H, –OCH3), 5.74
(s, 1H, –CHOH), 6.83 (d, J = 8.4, 2H, -Ar), 7.20–7.35 (m, 7H, -Ar); 13C
NMR (75 MHz) d 55.6, 76.1, 114.1, 126.6, 127.6, 128.1, 128.6, 136.4,
144.2, 159.2
4.13. 2-Methoxyphenyl(phenyl)methanol (3aj) [20]
4.21. 3-Phenylcyclohexanone (5aa) [26]
1H NMR d 3.14 (brs, 1H, –OH), 3.73 (s, 3H, –OCH3), 6.01 (s, 1H,
–CHOH), 6.81–6.92 (m, 2H, -Ar), 7.19–7.36 (m, 7H, -Ar); 13C NMR
(75 MHz) d 55.3, 71.9, 110.5, 120.6, 126.3, 126.9, 127.6, 127.9,
128.5, 131.8, 143.1, 156.4.
1H NMR (CDCl3, 300 MHz) d 1.70–1.92 (m, 2H), 2.07–2.19 (m,
2H), 2.32–2.63 (m, 4H), 2.95–3.06 (m, 1H, –CHAr), 7.19–7.24 (m,
3H, -Ar), 7.29–7.34 (m, 2H, -Ar) 13C NMR (75 MHz) d 25.9, 33.1,
41.5, 49.2, 126.8, 126.9, 128.9, 144.5, 211.0.
4.14. Ethyl mandelate (3ak)
4.22. 3-Phenylcyclopentanone (5ab) [26]
1H NMR (CDCl3): d 1.19 (t, J = 7.2 Hz, 3H, –OCH2CH3), 3.61 (brs,
1H, –OH), 4.08–4.28 (m, 2H, –OCH2CH3), 5.13 (s, 1H, –CHOH), 7.26–
7.42 (m, 5H, -Ar); 13C NMR (75 MHz) d 14.0, 62.1, 126.3, 128.1,
128.3, 138.2, 173.3.
1H NMR (CDCl3, 300 MHz) d 1.88–2.02 (m, 1H), 2.19–2.47 (m,
4H), 2.63 (dd, J = 18.6 and 7.5 Hzs, 1H), 3.32–3.44 (m, 1H,
–CHAr), 7.18–7.23 (m, 3H, -Ar), 7.29–7.33 (m, 2H, -Ar); 13C
NMR (CDCl3, 75 MHz) d 31.5, 39.2, 42.5, 46.1, 126.9, 128.8,
143.2, 218.5.
4.15. 4-Methoxyphenyl(2-naphthyl)methanol (3bf)[21]
1H NMR (CDCl3, 300 MHz) d 2.46 (s, 1H, –OH), 3.79 (s, 3H,
–OCH3), 5.94 (s, 1H, –CHOH), 6.86 (d, J = 8.7, 2H, -Ar), 7.25–7.49
(m, 5H, -Ar), 7.77–7.89 (m, 4H, -Ar); 13C NMR (75 MHz) d 55.3,
75.8, 113.8, 124.6, 124.6, 125.8, 126.0, 127.5, 127.9, 128.0, 128.1,
132.6, 133.1,135.8, 141.1, 158.9.
4.23. 3-Phenylcycloheptanone (5ac) [26]
1H NMR (CDCl3, 300 MHz) d 1.44–1.57 (m, 1H), 1.64–1.79 (m,
2H), 1.95–2.12 (m, 3H), 2.59–2.66 (m, 3H), 2.88–2.97 (m, 2H),
7.15–7.21 (m, 3H, -Ar), 7.26–7.31 (m, 2H, -Ar); 13C NMR (CDCl3,
75 MHz) d 24.5, 29.6, 39.5, 43.0, 44.3, 51.5, 126.6, 128.8, 128.9,
147.1, 213.5.
4.16. 2-Methoxyphenyl(2-naphthyl)methanol (3cf) [10b]
1H NMR (CDCl3, 300 MHz) d 3.14 (brs, 1H, –OH), 3.78 (s, 3H,
–CH3), 6.21 (d, J = 4.2, 1H, –CHOH), 6.86–6.94 (m, 2H, -Ar), 7.21–
7.27 (m, 2H, -Ar), 7.39–7.48 (m, 3H, -Ar), 7.75–7.85 (m, 4H, -Ar);
13C NMR (75 MHz) d 55.3, 72.1, 110.6, 120.6, 124.7, 124.8, 125.4,
125.7, 127.4, 127.6, 127.80, 127.84, 128.6, 131.6, 132.5, 133.0,
140.4, 156.5.
4.24. 1,3,3-Triphenyl-1-propanone (5ad) [26]
1H NMR (CDCl3, 300 MHz) d 3.70 (d, J = 7.2 Hz, 2H, –COCH2),
4.81 (t, J = 7.2 Hz, 1H, –CHAr), 7.10–7.26 (m, 10H, -Ar), 7.34–7.50
(m, 3H, -Ar), 7.87–7.90 (m, 2H, -Ar); 13C NMR (CDCl3, 75 MHz) d
45.1, 46.4, 126.6, 128.0, 128.2, 128.8, 128.9, 133.4, 137.2, 144.4,
198.1.
4.17. 4-Methylphenyl(2-naphthyl)methanol (3df) [22]
4.25. 4,4-Diphenyl-2-butanone (5ae) [27]
1H NMR (CDCl3, 300 MHz) d 2.26 (brs, 1H, –OH), 2.32 (s, 3H,
–CH3), 5.95 (s, 1H, –CHOH), 7.13 (d, J = 8.2 Hz, 2H, -Ar), 7.23–7.29
(m, 2H, -Ar), 7.29–7.48 (m, 3H, -Ar), 7.75–7.87 (m, 4H, -Ar); 13C
NMR (75 MHz) d 21.5, 76.5, 125.0, 125.1, 126.1, 126.4, 126.9,
127.9, 128.3, 128.5, 129.5, 133.1, 133.5, 137.6, 141.0, 141.5.
1H NMR (CDCl3, 300 MHz) d 2.07 (s, 3H, –COCH3), 3.17 (d,
J = 7.5 Hz, 2H, –COCH2), 4.58 (t, J = 7.5 Hz, 1H, –CHAr), 7.13–7.29
(m, 10H, -Ar); 13C NMR (CDCl3, 75 MHz) d 31.0, 46.4, 50.0, 126.7,
128.0, 128.8, 144.1, 206.9.