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165 (6), 126 (9); IR (neat) 3430, 3105, 1625, 1595, 1524,
1490, 1442, 1347, 1175, 1107, 878, 795, 765, 723,
698 cmÀ1. Anal. Calcd. for C21H14F3NO2: C, 68.29; H,
3.82. Found: C, 68.02; H, 3.88.
(CDCl3) d À56.27 (s, 3F); MS, m/z (relative intensity)
276 (Mþ, 100), 261 (49), 241 (24), 192 (28), 183 (15),
165 (2), 129 (10), 115 (4), 77 (3), 51 (9); IR (KBr) 3056,
2923, 1638, 1605, 1488, 1444, 1327, 1265, 1222, 1172,
1113, 1075, 815, 760, 699 cmÀ1. Anal. Calcd. for C17H15F3:
C, 73.90; H, 5.47. Found: C, 73.69; H, 5.34.
1
16k: oil; H NMR (CDCl3) d 7.41–6.82 (m, 14H); 19F
NMR (CDCl3) d À56.19 (s, 3F), À63.35 (s, 3F); MS, m/z
(relative intensity) 392 (Mþ, 100), 373 (7), 351 (11), 323
(17), 283 (23), 253 (15); IR (neat) 3025, 1492, 1445, 1348,
1224, 1173, 1143, 1113, 878, 795, 765, 701 cmÀ1. Anal.
Calcd. for C22H14F6: C, 67.35; H, 3.60. Found: C, 67.01; H,
3.53.
17a: oil; 1H NMR (CDCl3) d 7.57–7.13 (m, 10H), 1.79 (q,
J ¼ 2:2 Hz, 3H); 19F NMR (CDCl3) d À56.30 (s, 3F); MS,
m/z (relative intensity) 262 (Mþ, 100), 247 (35), 227 (36),
193 (46), 178 (59), 165 (10), 115 (25), 91 (11), 77 (10); IR
(neat) 3060, 2962, 2853, 1578, 1445, 1325, 1260, 1215,
1156, 1110, 1014, 935, 760, 700 cmÀ1. Anal. Calcd. for
C16H13F3: C, 73.27; H, 5.00. Found: C, 73.02; H, 4.87.
17b: oil; 1H NMR (CDCl3) d 7.39–6.92 (m, 9H), 1.81 (q,
J ¼ 2:2 Hz, 3H); 19F NMR (CDCl3) d À56.30 (s, 3F); MS,
m/z (relative intensity) 342 (Mþ þ 2, 65), 340 (Mþ, 66), 246
(51), 221 (8), 192 (100), 133 (8), 115 (11); IR (neat) 3146,
2951, 2927, 1711, 1349, 1249, 1153, 1127, 1035, 749,
695 cmÀ1. Anal. Calcd. for C16H12BrF3: C, 56.33; H,
3.55. Found: C, 56.04; H, 3.63.
17c: oil; 1H NMR (CDCl3) d 7.26–6.84 (m, 9H), 3.78 (s,
3H), 1.84 (q, J ¼ 2:2 Hz, 3H); 19F NMR (CDCl3) d À56.89
(s, 3F); MS, m/z (relative intensity) 292 (Mþ, 100), 261 (4),
234 (3), 208 (22), 178 (8), 165 (13), 145 (8), 115 (17); IR
(neat) 3038, 2956, 2924, 2871, 1513, 1463, 1249, 1161,
1117, 1040, 757, 697 cmÀ1. Anal. Calcd. for C17H15F3O: C,
69.85; H, 5.17. Found: C, 69.59; H, 5.05.
17d: mp 61–62 8C; 1H NMR (CDCl3) d 7.34–7.23 (m, 9H),
2.40 (s, 3H), 1.88 (q, J ¼ 2:2 Hz, 3H); 19F NMR (CDCl3) d
À56.39 (s, 3F); MS, m/z (relative intensity) 276 (Mþ, 100),
261 (59), 241 (52), 202 (59), 192 (89), 165 (19), 115 (18), 77
(10); IR (KBr) 3023, 2957, 1331, 1260, 1207, 1162, 1110,
1026, 801, 763, 699 cmÀ1. Anal. Calcd. for C17H15F3: C,
73.90; H, 5.47. Found: C, 73.61; H, 5.35.
1
18a: oil; H NMR (CDCl3) d 7.42–7.26 (m, 10H); 19F
NMR (CDCl3) d À64.87 (d, J ¼ 9:9 Hz, 3F), À129.29 (q,
J ¼ 9:8 Hz, 1F); MS, m/z (relative intensity) 266 (Mþ, 100),
245 (15), 196 (85), 177 (17), 165 (29), 98 (15), 51 (14); IR
(CCl4) 3062, 2959, 2927, 1731, 1549, 1344, 1282, 1195,
1143, 1100, 1010, 699 cmÀ1. Anal. Calcd. for C15H10F4: C,
67.67; H, 3.79. Found: C, 67.34; H, 3.75.
1
18b: oil; H NMR (CDCl3) d 7.55–7.00 (m, 9H); 19F
NMR (CDCl3) d À64.95 (d, J ¼ 9:8 Hz, 3F), À128.16 (q,
J ¼ 9:9 Hz, 1F); MS, m/z (relative intensity) 346 (Mþ þ 2,
31), 344 (Mþ, 32), 245 (20), 196 (100); IR (CCl4) 3082,
3033, 2958, 2927, 1585, 1550, 1490, 1338, 1280, 1206,
1195, 1145, 1101, 1075, 1012, 700 cmÀ1. Anal. Calcd. for
C15H9BrF4: C, 52.20; H, 2.63. Found: C, 52.01; H, 2.59.
18c: oil; 1H NMR (CDCl3) d 7.68–7.12 (m, 9H); 19F NMR
(CDCl3) d À64.92 (d, J ¼ 9:9 Hz, 3F), À128.35 (q,
J ¼ 9:9 Hz, 1F); MS, m/z (relative intensity) 302 (Mþ þ 2,
33), 300 (Mþ, 100), 265 (17), 245 (13), 196 (79). Anal. Calcd.
for C15H9ClF4: C, 59.92; H, 3.02. Found: C, 59.53; H, 3.05.
1
18d: oil; H NMR (CDCl3) d 7.43–6.94 (m, 9H); 19F
NMR (CDCl3) d À64.83 (d, J ¼ 10:0 Hz, 3F), À112.18 (s,
1F), À129.35 (q, J ¼ 9:9 Hz, 1F); MS, m/z (relative inten-
sity) 284 (Mþ, 100), 214 (46), 183 (34), 107 (11). Anal.
Calcd. for C15H9F5: C, 63.34; H, 3.19. Found: C, 63.03; H,
3.14.
18e: oil; 1H NMR (CDCl3) d 7.42–6.81 (m, 9H), 3.80 (s,
3H); 19F NMR (CDCl3) d À64.60 (d, J ¼ 10:1 Hz, 3F),
À131.01 (q, J ¼ 10:0 Hz, 1F); MS, m/z (relative intensity)
296 (Mþ, 100), 277 (4), 226 (7), 212 (10), 195 (35), 183 (31),
152 (6); IR (CCl4) 3061, 3004, 2957, 2930, 2855, 1659,
1606, 1564, 1512, 1463, 1342, 1287, 1254, 1194, 1140,
1098, 1038, 700 cmÀ1. Anal. Calcd. for C16H12F4O: C,
64.86; H, 4.08. Found: C, 64.73; H, 4.02.
17e: mp 110–112 8C; 1H NMR (CDCl3) d 8.36–8.28 (m,
4H), 7.58–7.21 (m, 5H), 1.91 (q, J ¼ 2:1 Hz, 3H); 19F NMR
(CDCl3) d À55.97 (s, 3F); MS, m/z (relative intensity) 307
(Mþ, 100), 246 (37), 192 (49), 165 (16), 151 (5), 115 (6), 77
(12), 51 (11); IR (KBr) 3080, 2994, 2359, 1653, 1520, 1350,
1264, 1216, 1162, 1106, 1013, 849, 765, 698 cmÀ1. Anal.
Calcd. for C16H12F3NO2: C, 62.54; H, 3.94. Found: C,
62.29; H, 3.85.
18f: oil; 1H NMR (CDCl3) d 7.42–7.00 (m, 9H), 2.35 (s,
3H); 19F NMR (CDCl3) d À64.80 (d, J ¼ 10:0 Hz, 3F),
À130.01 (q, J ¼ 9:9 Hz, 1F); MS, m/z (relative intensity)
280 (Mþ, 100), 265 (24), 245 (12), 211 (26), 196 (86), 179
(27), 133 (5), 128 (6), 91 (11); IR (CCl4) 3063, 3028, 2960,
2928, 2873, 2857, 1730, 1579, 1549, 1463, 1379, 1340,
1284, 1206, 1140, 1121, 1073, 1006, 977, 702 cmÀ1. Anal.
Calcd. for C16H12F4: C, 68.57; H, 4.32. Found: C, 68.70; H,
4.24.
17f: oil; 1H NMR (CDCl3) d 7.33–7.15 (m, 9H), 3.40 (s,
3H), 1.86 (q, J ¼ 2:0 Hz, 3H); 19F NMR (CDCl3) d À56.27
(s, 3F); MS, m/z (relative intensity) 292 (Mþ, 100), 277 (21),
261 (9), 249 (4), 223 (10), 208 (20), 183 (9), 165 (20), 145
(5), 115 (12); IR (neat) 3022, 2958, 1600, 1580, 1487, 1334,
1248, 1155, 1117, 1031, 960, 732, 699 cmÀ1. Anal. Calcd.
for C17H15F3O: C, 69.85; H, 5.17. Found: C, 69.59; H, 5.06.
1
18g: oil; H NMR (CDCl3) d 8.31–7.26 (m, 9H); 19F
NMR (CDCl3) d À64.90 (d, J ¼ 9:8 Hz, 3F, one isomer),
À65.10 (q, J ¼ 9:9 Hz, 3F, other isomer), À125.30 (q,
J ¼ 9:7 Hz, 1F, one isomer), À126.30 (q, J ¼ 9:8 Hz, 1F,
other isomer); MS, m/z (relative intensity) 311 (Mþ, 100),
264 (18), 245 (6), 225 (5), 214 (5), 196 (33), 183 (7); IR
(CCl4) 3060, 3028, 2958, 2926, 2855, 1728, 1665, 1603,
1527, 1494, 1447, 1341, 1284, 1261, 1196, 1149, 1103,
1
17g: mp 50–52 8C; H NMR (CDCl3) d 7.33–7.15 (m,
9H), 2.40 (s, 3H), 1.85 (q, J ¼ 2:1 Hz, 3H); 19F NMR