1534
Brath et al.:
124.8, 121.6, 113.5, 113.1, 54.1. GC-MS (EI), m/z (%): 466 (100) [M• +], 313 (26), 326 (16).
(RS)-1J: m .p. 135–138 °C. HPLC: Ch iralcel Daicel OD-H colum n , eluen t n-h eptan e with 20%
DME, tem perature 21 °C, flow rate 1.0 m l/m in , pressure 47 bar, detector (UV) λ = 280 n m ;
k′: 2.09 (S)-1J, 2.67 (R)-1J.
(R)-2,2′-Bis[4-(dimethylamino)phenyl]-1,1′-binaphthalene (1K). Wh ite solid, m .p. 195–198 °C,
[α ]2D0 +12.1 (c 0.01, CHCl3), >99% e.e. (determ in ed by HPLC), RF 0.29 (h exan es–eth yl acetate,
4:1). UV-VIS (c 1.30 × 10–5 M, MeOH (log ε)): 222 (4.41), 290 (3.97). IR (CHCl3): 1610, 1520,
1420, 1410, 1350, 1220, 925, 700. 1H NMR (300 MHz, CDCl3): 7.90 d, 2 H, 3J = 8.2; 7.9 d,
2 H, 3J = 8.5; 7.48–7.35 m , 6 H, 3J = 8.5; 7.28 m , 2 H, 3J = 6.7; 6.42 d, 4 H, 3J = 8.8; 6.29 d,
4 H, 3J = 8.8; 2.81 s, 12 H (CH3). 13C NMR (75 MHz, CDCl3): 149.1, 139.0, 134.8, 134.3,
132.2, 130.4, 130.0, 129.1, 128.1, 127.8, 127.6, 126.4, 125.2, 111.8, 40.8. For C36H32N2
(492.7) calculated: 87.77% C, 6.55% H, 5.69% N; foun d: 87.22% C, 6.57% H, 5.55% N.
(RS)-1K: m .p. 270–280 °C with decom position . HPLC: Ch iralcel Daicel OD-H colum n , eluen t
n-h exan e with 10% propan -2-ol, tem perature 16 °C, flow rate 0.5 m l/m in , pressure 18 bar,
detector (UV) λ = 254 n m ; k′: 3.97 (S)-1K, 4.91 (R)-1K.
(R)-2,2′-Bis(4-cyanophenyl)-1,1′-binaphthalene (1L). Wh ite solid, m .p. 86–90 °C, [α ]2D0 +105.8
(c 0.01, CHCl3), >99% e.e. (determ in ed by HPLC), RF 0.15 (h exan es–eth yl acetate, 4:1).
UV-VIS (c 9.98 × 10–5 M, MeOH (log ε)): 222 (4.83), 272 (4.70). IR (CHCl3): 2220, 1600,
1490, 1440, 1200, 1030, 920, 840, 820, 690. 1H NMR (300 MHz, CDCl3): 8.00 d, 2 H, 3J =
8.2; 7.98 d, 2 H, 3J = 8.2; 7.58 d, 2 H, 3J = 8.2; 7.40 2 × d, 2 × 2 H; 7.33 d, 2 H, 3J = 8.2; 7.19
dd, 4 H, 3J = 8.2; 6.50 d, 4 H, 3J = 8.2. 13C NMR (75 MHz, CDCl3): 146.0, 137.8, 134.4,
134.1, 132.9, 131.3, 129.8, 129.4, 128.7, 127.7, 127.6, 127.4, 126.8, 119.0, 110.4. GC-MS
(EI), m/z (%): 456 (100) [M+], 351 (22), 338 (10). (RS)-1L: 300–310 °C with decom position .
HPLC: Ch iralcel Daicel OD-H colum n , eluen t n-h exan e with 10% propan -2-ol, tem perature
16 °C, flow rate 0.75 m l/m in , pressure 27 bar, detector (UV) λ = 254 n m ; k′: 5.23 (S)-1L, 6.78
(R)-1L.
(S)-2,2′-Di-2-thienyl-1,1′-binaphthalene (1M). Wh ite off solid, m .p. 155–159 °C, [α ]2D1 +15.7
(c 1, CHCl3), >99% e.e. (determ in ed by HPLC), RF 0.32 (h exan es–eth yl acetate, 10:1). UV-VIS
(c 9.98 × 10–5 M, MeOH (log ε)): 222 (4.83), 272 (4.70), 302 (4.39). Spectral data were in
agreem en t with literature values29. For C28H20S2 (418.6) calculated: 80.35% C, 4.33% H,
15.32% S; foun d: 79.47% C, 4.04% H, 14.56% S. (RS)-1O: m .p: 195–200 °C (aceton e–water)
(lit.29 m .p. 204–206 °C). HPLC: Ch iralcel Daicel OD-H colum n , eluen t n-h eptan e with 1%
DME, tem perature 21°C, flow rate 1.0 m l/m in , pressure 47 bar, detector (UV) λ = 280 n m ; k′:
5.84 (S)-1M, 6.35 (R)-1M.
2-Phenyl-1,1′-binaphthalene (10G). Wh ite solid, m .p. 131–133 °C (lit.11 m .p. 133 °C), RF
0.52 (h exan es–ch loroform , 4:1). Spectral data were in agreem en t with literature values11
.
(R)-2-(4-Methylphenyl)-1,1′-binaphthalene (10H). Wh ite solid, m .p. 110–111 °C, [α ]2D2.5 –133
(c 1, CHCl3), >99% e.e. (determ in ed by HPLC), RF 0.52 (h exan es–ch loroform , 4:1). Spectral
data were in agreem en t with literature values11. (RS)-10H: m .p. 121–123 °C (lit.11 m .p.
123 °C). HPLC: Ch iralcel Daicel OD-H colum n , eluen t n-h exan e with 1% DME, tem perature
17 °C, flow rate 1.0 m l/m in , pressure 32 bar, detector (UV) λ = 254 n m ; k′: 3.03 (R)-10H,
4.29 (S)-10H.
2-(2-Methoxyphenyl)-1,1′-binaphthalene (10I). Wh ite solid, m .p. 54–58 °C, RF 0.38 (h exan es–
ch loroform , 4:1). UV-VIS (c 5.08 × 10–5 M, MeOH (log ε)): 222 (4.97), 285 (3.14). IR (CHCl3):
1590, 1580, 1490, 1460, 1430, 1370, 1200, 1120, 1020, 920, 700. 1H NMR (50 °C, 300 MHz,
CDCl3): 7.99 d, 1 H, 3J = 8.2; 7.95 d, 1 H, 3J = 8.2; 7.80 d, 1 H, 3J = 8.2; 7.73 d, 1 H, 3J = 8.2;
7.57 d, 1 H, 3J = 8.2; 7.55–7.15 m , 9 H, 3J = 8.2; 7.0 dd, 1 H, 3J = 8.2, 7.7; 6.60 br, 2 H;
Collect. Czech. Chem. Commun. (Vol. 69) (2004)