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J.-W. Huang, M. Shi / Tetrahedron 60 (2004) 2057–2062
158.79; MS (EI) m/z: 394 (Mþ) (8), 267 (28), 227 (9), 205
(13), 159 (19), 121 (23), 84 (100); HRMS (EI) Calcd for
C18H19IO2: 394.0430. Found: 394.0446.
7.20 (m, 8H, ArH); 19F NMR (282 MHz, TMS, CDCl3):
2115.47, 2115.02; MS (EI) m/z: 322 (Mþ) (64), 229 (100),
214 (30), 147 (82), 133 (54), 109 (85); HRMS (EI) Calcd for
C16H13BrF2: 322.0169. Found: 322.0177.
3.2.7. 1-[4-Chloro-1-(4-methylphenyl)but-1-enyl]-4-
methylbenzene (2g). This compound was obtained as a
colorless oil in 98% yield. IR (neat): n 3023, 2921, 1606,
3.2.12. 1-Fluoro-4-[1-(4-fluorophenyl)-4-iodobut-1-
enyl]benzene (2l). This compound was obtained as a
colorless oil in 95% yield. IR (neat): n 3043, 2958, 1601,
1
1511, 1448, 1295, 1110, 1021 cm21; H NMR (300 MHz,
1
TMS, CDCl3): d 2.32 (s, 3H, CH3), 2.37 (s, 3H, CH3), 2.57
(td, J¼7.2, 7.2 Hz, 2H, CH2), 3.54 (t, J¼7.2 Hz, 2H, CH2),
6.03 (t, J¼7.2 Hz, 1H, CvCH), 7.03–7.19 (m, 8H, ArH);
13C NMR (75 MHz, TMS, CDCl3): d 21.05, 21.21, 32.92,
44.43, 123.62, 127.17, 128.78, 128.94, 129.56, 136.72,
136.78, 136.97, 139.51, 144.12; MS (EI) m/z: 270 (Mþ)
(14), 221 (25), 210 (46), 119 (100), 91 (41); HRMS (EI)
Calcd for C18H19Cl: 270.1175. Found: 270.1197.
1508, 1225, 1158, 1094, 1014 cm21; H NMR (300 MHz,
TMS, CDCl3): d 2.67 (td, J¼7.2, 7.2 Hz, 2H, CH2), 3.19 (t,
J¼7.2 Hz, 2H, CH2), 5.95 (t, J¼7.2 Hz, 1H, CvCH), 6.93–
7.20 (m, 8H, ArH); 19F NMR (282 MHz, TMS, CDCl3):
2115.47, 2114.99; 13C NMR (75 MHz, TMS, CDCl3): d
5.46, 33.14, 114.89, 115.18, 115.23, 115.51, 127.92, 127.95,
128.78, 128.88, 131.20, 131.31, 135.20, 138.13, 138.85,
141.79, 160.39, 163.66, 163.86; MS (EI) m/z: 370 (Mþ)
(24), 243 (100), 227 (11), 214 (14), 201 (14), 147 (93), 109
(95); HRMS (EI) Calcd for C16H13F2I: 370.0030. Found:
370.0036.
3.2.8. 1-[4-Bromo-1-(4-methylphenyl)but-1-enyl]-4-
methylbenzene (2h). This compound was obtained as a
colorless oil in 96% yield. IR (neat): n 3022, 2920, 1609,
1
1511, 1445, 1267, 1207, 1020 cm21; H NMR (300 MHz,
3.2.13. 4,4-Bis(4-chlorophenyl)-1-chloro-but-3-ene (2m).
This compound was obtained as a colorless oil in 91% yield.
IR (neat): n 3030, 2956, 2925, 1592, 1492, 1401,
;
1091 cm21 1H NMR (300 MHz, TMS, CDCl3): d 2.57
(td, J¼6.6, 6.6 Hz, 2H, CH2), 3.58 (t, J¼6.6 Hz, 2H, CH2),
6.11 (t, J¼6.6 Hz, 1H, CvCH), 7.09–7.38 (m, 8H, ArH);
13C NMR (75 MHz, TMS, CDCl3): d 33.03, 44.36, 126.20,
128.64, 128.77, 128.99, 131.31, 133.63, 133.71, 137.77,
140.41, 142.49; MS (EI) m/z: 310 (Mþ), 275, 261, 226, 191,
163; HRMS (EI) Calcd for C16H13Cl3: 310.0083. Found:
310.0047.
TMS, CDCl3): d 2.30 (s, 3H, CH3), 2.36 (s, 3H, CH3), 2.66
(td, J¼7.2, 7.2 Hz, 2H, CH2), 3.38 (t, J¼7.2 Hz, 2H, CH2),
6.00 (t, J¼7.2 Hz, 1H, CvCH), 7.03–7.18 (m, 8H, ArH);
13C NMR (75 MHz, TMS, CDCl3): d 21.04, 21.21, 32.77,
32.93, 124.62, 127.15, 128.77, 128.93, 129.52, 136.66,
136.75, 136.95, 139.46, 143.96; MS (EI) m/z: 316 (Mþ)
(73), 221 (100), 205 (42), 143 (97), 129 (55), 105 (60);
HRMS (EI) Calcd for C18H19Br: 314.0670. Found:
314.0653.
3.2.9. 1-[4-Iodo-1-(4-methylphenyl)but-1-enyl]-4-
methylbenzene (2i). This compound was obtained as a
colorless oil in 96% yield. IR (neat): n 3021, 2919, 1609,
3.2.14. 4,4-Bis-(4-chlorophenyl)-1-bromo-but-3-ene (2n).
This compound was obtained as a colorless oil in 95% yield.
IR (neat): n 3030, 2963, 1661, 1590, 1491, 1268,
1511, 1444, 1239, 1169, 1110, 1020 cm21 1H NMR
;
(300 MHz, TMS, CDCl3): d 2.30 (s, 3H, CH3), 2.37 (s,
3H, CH3), 2.66 (td, J¼7.2, 7.2 Hz, 2H, CH2), 3.15 (t,
J¼7.2 Hz, 2H, CH2), 5.94 (t, J¼7.2 Hz, 1H, CvCH), 7.02–
7.18 (m, 8H, ArH); 13C NMR (75 MHz, TMS, CDCl3): d
6.78, 21.06, 21.22, 33.39, 126.56, 127.16, 128.77, 128.90,
129.51, 136.71, 136.75, 136.93, 139.50, 143.48; MS (EI)
m/z: 362 (Mþ) (14), 235 (68), 219 (17), 205 (20), 143 (100),
128 (34), 105 (72); HRMS (EI) Calcd for C18H19I:
362.0531. Found: 362.0500.
1091 cm21 1H NMR (300 MHz, TMS, CDCl3): d 2.65
;
(td, J¼7.2, 7.2 Hz, 2H, CH2), 3.42 (t, J¼6.6 Hz, 2H, CH2),
6.06 (t, J¼7.2 Hz, 1H, CvCH), 7.08–7.37 (m, 8H, ArH);
13C NMR (75 MHz, TMS, CDCl3): d 40.42, 41.67, 126.37,
128.26, 128.31, 128.46, 130.96, 131.26, 133.37, 137.39,
140.04, 141.97; MS (EI) m/z: 354 (Mþ), 261, 250, 235, 226,
202, 191, 163; HRMS (EI) Calcd for C16H13BrCl2:
353.9578. Found: 353.9569.
3.2.15. 4,4-Bis(4-chlorophenyl)-1-iodo-but-3-ene (2o).
This compound was obtained as a colorless oil in 98%
yield. IR (neat): n 3030, 2957, 1591, 1491, 1400,
3.2.10. 1-[4-Chloro-1-(4-fluorophenyl)but-1-enyl]-4-
fluorobenzene (2j). This compound was obtained as a
colorless oil in 97% yield. IR (neat): n 2958, 2926, 1602,
1508, 1445, 1409, 1297, 1225, 1094, 1015 cm21; 1H NMR
(300 MHz, TMS, CDCl3): d 2.56 (td, J¼6.8, 7.2 Hz, 2H,
CH2), 3.57 (t, J¼6.8 Hz, 2H, CH2), 6.04 (t, J¼7.2 Hz, 1H,
CvCH), 6.92–7.20 (m, 8H, ArH); 19F NMR (282 MHz,
TMS, CDCl3): 2115.47, 2115.02; MS (EI) m/z: 278 (Mþ)
(55), 229 (100), 214 (20), 147 (14), 133 (41), 109 (30);
HRMS (EI) Calcd for C16H13ClF2: 278.0674. Found:
278.0664.
1091 cm21 1H NMR (300 MHz, TMS, CDCl3): d 2.65
;
(td, J¼7.2, 7.2 Hz, 2H, CH2), 3.17 (t, J¼7.2 Hz, 2H, CH2),
5.99 (t, J¼7.2 Hz, 1H, CvCH), 7.07–7.36 (m, 8H, ArH);
13C NMR (75 MHz, TMS, CDCl3): d 5.20, 33.08, 128.35,
128.49, 128.57, 128.66, 128.75, 130.97, 133.31, 137.46,
140.12, 141.57; MS (EI) m/z: 402 (Mþ), 275, 250, 204, 163;
HRMS (EI) Calcd for C16H13Cl2I: 401.9439. Found:
401.9482.
3.2.16. 1-(4-Bromo-1-phenyl-but-1-enyl)-4-methoxy-
benzene (2p). This compound was obtained as a colorless
oil (Z/E-mixture, 2:1) in 100% yield. IR (neat): n 3028,
2958, 2835, 1606, 1575, 1510, 1493, 1443, 1247, 1179,
3.2.11. 1-[4-Bromo-1-(4-fluorophenyl)but-1-enyl]-4-
fluorobenzene (2k). This compound was obtained as a
colorless oil in 92% yield. IR (neat): n 2968, 1602, 1508,
1
1
1225, 1158, 1094, 1015 cm21; H NMR (300 MHz, TMS,
1034 cm21; H NMR (300 MHz, TMS, CDCl3): for Z- or
CDCl3): d 2.67 (td, J¼7.2, 7.3 Hz, 2H, CH2), 3.43 (t,
E-2p: d 2.60–2.75 (m, 2H, CH2), 3.38–3.43 (m, 2H, CH2),
3.78 (s, 3H, OCH3), 5.99 (t, J¼7.2 Hz, 1H), 6.78–7.38 (m,
J¼7.2 Hz, 2H, CH2), 6.02 (t, J¼7.3 Hz, 1H, CvCH), 6.93–