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Y. Li et al. / Tetrahedron 72 (2016) 5684e5690
4.2.4. 4-(1,1,1-Trifluoroprop-2-en-2-yl) biphenyl (3d). White solid.
123.1 (q, J¼272.2 Hz), 121.4 (q, J¼5.8 Hz), 52.1. 19F NMR (470.0 MHz)
Rf¼0.7 (petroleum ether); 1H NMR (500 MHz, CDCl3)
d
7.61 (t, 4H,
d
ꢁ64.8 (s, 3F).
J¼5.0 Hz), 7.54 (d, 2H, J¼10.0 Hz), 7.45 (t, 2H, J¼10.0 Hz), 7.37 (t, 1H,
IR (KBr): 1730, 1442, 1353, 1280, 1171, 1132, 1098, 953, 768 cmꢁ1
HRMS (ESI): calcd for [M]þ 230.0555; found: 230.0550.
.
J¼10.0 Hz), 5.98 (d, 1H, J¼5.0 Hz), 5.83 (d, 1H, J¼5.0 Hz). 13C NMR
(125 MHz, CDCl3)
d
141.8, 140.3, 138.7 (q, J¼35.9 Hz), 132.5, 138.8 (q,
J¼35.9 Hz), 131.3 (d, J¼7.4 Hz), 122.3 (d, J¼7.4 Hz), 119.1 (qd,
4.2.11. 3-(1,1,1-Trifluoroprop-2-en-2-yl)benzonitrile (3k). Colorless
J¼272.6 Hz, J¼41.6 Hz), 114.3, 111.0, 55.3. 19F NMR (470.0 MHz)
oil. Rf¼0.7 (petroleum ether); 1H NMR (500 MHz, CDCl3)
d 7.74 (s,
d
ꢁ64.6 (s, 3F).
1H), 7.70e7.57 (m, 2H), 7.53 (t, 1H, J¼7.5 Hz), 6.09 (d, 1H, J¼1.5 Hz),
IR (KBr): 1610, 1521, 1366, 1255, 1184, 1152, 1088, 966, 857 cmꢁ1
HRMS (ESI): calcd for [M]þ 248.0813; found: 248.0810.
.
5.85 (q, 1H, J¼1.5 Hz). 13C NMR (125 MHz, CDCl3)
d 137.3 (q,
J¼30.9 Hz), 134.8, 132.4, 131.7, 131.0, 123.9, 122.8 (q, J¼272.3 Hz),
122.5 (q, J¼6.0 Hz), 118.2,113.1. 19F NMR (470.0 MHz)
ꢁ65.0 (s, 3F).
d
4.2.5. 4-(1,1,1-Trifluoroprop-2-en-2-yl)benzonitrile (3e). Colorless
IR (KBr): 1612, 1575, 1464,1353, 1224, 1168, 1130, 956 cmꢁ1
.
oil. Rf¼0.7 (petroleum ether); 1H NMR (500 MHz, CDCl3)
d
7.70 (d,
HRMS (ESI): calcd for [M]þ 197.0452; found: 197.0450.
2H, J¼5.0 Hz), 7.58 (d, 2H, J¼5.0 Hz), 6.11 (d, 1H, J¼1.5 Hz), 5.88 (q,
1H, J¼1.5 Hz). 13C NMR (125 MHz, CDCl3)
d
137.9, 137.7 (q,
4.2.12. 1-Nitro-4-(1,1,1-trifluoroprop-2-en-2-yl)benzene
(3l). Colorless oil. Rf¼0.7 (petroleum ether); 1H NMR (500 MHz,
J¼30.6 Hz), 132.4, 128.1, 122.8 (q, J¼272.3 Hz), 122.8 (q, J¼5.6 Hz),
118.2, 112.9. 19F NMR (470.0 MHz)
IR (KBr): 1610, 1513, 1404, 1352, 1263, 1196, 1177, 1127, 1077,
d
ꢁ65.0 (s, 3F).
CDCl3)
d
7.39 (d, 2H, J¼8.0 Hz), 7.24 (d, 2H,J¼8.5 Hz), 5.90 (d, 1H,
J¼1.5 Hz), 5.73 (q, 1H, J¼1.5 Hz), 2.92 (m, 3H), 1.26 (s, 3H), 1.25 (s,
1021 cmꢁ1
.
3H). 13C NMR (125 MHz, CDCl3)
d
149.8, 138.9 (q, J¼29.6 Hz), 131.1,
HRMS (ESI): calcd for [M]þ 197.0452; found: 197.0450.
127.3, 126.9, 123.5 (q, J¼231.0 Hz), 119.6 (q, J¼5.8 Hz), 33.9, 23.7. 19
F
NMR (470.0 MHz)
d
ꢁ64.7 (s, 3F).
4.2.6. 4-(1,1,1-Trifluoroprop-2-en-2-yl)benzaldehyde (3f). Colorless
IR (KBr): 1645, 1536, 1415, 1353, 1194, 1174, 1127, 952, 906 cmꢁ1
.
oil. Rf¼0.7 (petroleum ether); 1H NMR (500 MHz, CDCl3)
d
10.04 (s,
HRMS (ESI): calcd for [M]þ 217.0351; found: 217.0350.
1H), 7.91 (d, 2H, J¼8.5 Hz), 7.63 (d, 2H, J¼8.5 Hz), 6.09 (d, 1H,
J¼1.0 Hz), 5.90 (q, 1H, J¼1.0 Hz). 13C NMR (125 MHz, CDCl3)
d
191.6,
4.2.13. 1-Methoxy-2-(1,1,1-trifluoroprop-2-en-2-yl)benzene
(3m). Colorless oil. Rf¼0.7 (petroleum ether); 1H NMR (500 MHz,
139.3, 138.2 (q, J¼30.5 Hz), 136.5, 129.9, 128.0, 123.0 (q, J¼272.3 Hz),
122.4 (q, J¼5.6 Hz). 19F NMR (470.0 MHz)
d
ꢁ64.6 (s, 3F).
CDCl3)
d
7.36e7.32 (m, 1H), 7.21 (d, 1H, J¼6.5 Hz), 6.94 (q, 1H,
IR (KBr): 1707, 1610, 1571, 1413, 1354, 1193, 1179, 1129, 1080,
J¼6.5 Hz), 6.07 (d, 1H, J¼1.5 Hz), 5.83 (q, 1H, J¼1.5 Hz), 3.79 (s, 3H).
1018 cmꢁ1
.
13C NMR (125 MHz, CDCl3)
d
157.1, 136.1 (q, J¼31.4 Hz), 130.7, 130.2,
HRMS (ESI): calcd for [M]þ 200.0449; found: 200.0440.
129.5,123.3 (q, J¼5.3 Hz),123.1 (q, J¼271.8 Hz), 120.3, 111.3, 55.9. 19
F
NMR (470.0 MHz)
d
ꢁ65.8 (s, 3F).
4.2.7. 1-Nitro-4-(1,1,1-trifluoroprop-2-en-2-yl)benzene
(3g). Colorless oil. Rf¼0.7 (petroleum ether); 1H NMR (500 MHz,
IR (KBr): 1600, 1580, 1495, 1465, 1439, 1350, 1253, 1171, 1127,
1077 cmꢁ1
.
CDCl3)
d
8.25 (d, 2H, J¼9.5 Hz), 7.62 (d, 2H, J¼9.0 Hz), 6.15 (d, 1H,
HRMS (ESI): calcd for [M]þ 202.0605; found: 202.0601.
J¼1.0 Hz), 5.95 (q, 1H, J¼1.5 Hz). 13C NMR (125 MHz, CDCl3)
d 148.1,
139.7, 137.4 (q, J¼24.0 Hz), 124.8, 123.8, 122.8 (q, J¼272.3 Hz), 123.3
4.2.14. 1-Benzene-2-(1,1,1-trifluoroprop-2-en-2-yl)benzene
(3n). Colorless oil. Rf¼0.7 (petroleum ether); 1H NMR (500 MHz,
(q, J¼5.5 Hz). 19F NMR (470.0 MHz)
d
ꢁ64.8 (s, 3F).
IR (KBr): 1603, 1524, 1347, 1185, 1130, 1079, 956, 862, 841 cmꢁ1
.
CDCl3)
d
7.42 (t, 2H, J¼7.5 Hz), 7.37e7.29 (m, 4H), 7.28e7.22 (m, 3H),
HRMS (ESI): calcd for [M]þ 217.0351; found: 217.0350.
5.90 (s, 1H), 5.25 (s, 1H). 13C NMR (125 MHz, CDCl3)
d 141.8, 140.3,
138.7 (q, J¼35.9 Hz), 132.5, 128.8, 127.8, 127.7, 127.3, 127.1, 125.8, (q,
4.2.8. 1-Methoxy-3-(1,1,1-trifluoroprop-2-en-2-yl)benzene
(3h). Colorless oil. Rf¼0.7 (petroleum ether); 1H NMR (500 MHz,
J¼272.5 Hz), 120.2 (q, J¼5.8 Hz). 19F NMR (470.0 MHz)
d
ꢁ64.8 (s,
3F).
CDCl3)
d
7.28 (t, 1H, J¼8.0 Hz), 7.03 (d, 2H, J¼7.5 Hz), 6.98 (s, 1H),
IR (KBr): 1482, 1364, 1174, 1127, 1077, 952, 747, 702, 630 cmꢁ1
.
6.92 (dd, 1H, J¼8.5 Hz, 2.5 Hz), 5.94 (d, 1H, J¼1.0 Hz), 5.75 (q, 1H,
HRMS (ESI): calcd for [M]þ 248.0813; found: 248.0811.
J¼2.0 Hz), 3.81 (s, 3H). 13C NMR (125 MHz, CDCl3)
d 159.4, 138.9 (q,
J¼30.0 Hz), 135.0, 129.6, 123.3 (q, J¼272.4 Hz), 120.6 (q, J¼5.8 Hz),
4.2.15. 1,2-Dimethoxy-4-(1,1,1-trifluoroprop-2-en-2-yl)benzene
(3o). Colorless oil. Rf¼0.7 (petroleum ether); 1H NMR (500 MHz,
119.9, 114.3, 113.4, 55.2. 19F NMR (470.0 MHz)
IR (KBr): 1583, 1492, 1356, 1291, 1250, 1174, 1127, 1047, 950,
d
ꢁ64.9 (s, 3F).
CDCl3)
d
7.03 (d, 1H, J¼8.5 Hz), 6.96 (s, 1H), 6.86 (d, 1H, J¼8.5 Hz),
788 cmꢁ1
.
5.88 (d, 1H, J¼1.5 Hz), 5.71 (q, 1H, J¼2.0 Hz). 13C NMR (125 MHz,
HRMS (ESI): calcd for [M]þ 202.0605; found: 202.0601.
CDCl3)
d
149.6, 148.8, 138.5 (q, J¼29.6 Hz), 126.3, 123.4 (q,
J¼272.3 Hz), 120.3, 119.2 (q, J¼5.8 Hz), 111.0, 110.5, 55.9, 55.8. 19F
4.2.9. 1-Methyl-3-(1,1,1-trifluoroprop-2-en-2-yl)benzene
(3i). Colorless oil. Rf¼0.7 (petroleum ether); 1H NMR (500 MHz,
NMR (470.0 MHz)
d
ꢁ64.8 (s, 3F).
IR (KBr): 1606, 1583, 1524, 1468, 1365, 1347, 1259, 1159, 1124,
CDCl3)
d
7.28e7.18 (m, 4H), 5.92 (d, 1H, J¼1.5 Hz), 5.73 (q, 1H,
1026 cmꢁ1
.
J¼1.5 Hz), 2.36 (m, 3H). 13C NMR (125 MHz, CDCl3)
d
139.2 (q,
HRMS (ESI): calcd for [M]þ 232.0711; found: 232.0710.
J¼29.8 Hz), 138.3, 133.7, 129.7, 128.5, 128.1, 124.5, 122.3, 120.2 (q,
J¼5.8 Hz), 21.4. 19F NMR (470.0 MHz)
d
ꢁ64.8 (s, 3F).
4.2.16. 5-(1,1,1-Trifluoroprop-2-en-2-yl)benzo[d][1,3]dioxole
(3p). Colorless oil. Rf¼0.7 (petroleum ether); 1H NMR (500 MHz,
IR (KBr): 1598, 1486, 1355, 1198, 1180, 1088, 956, 766 cmꢁ1
.
HRMS (ESI): calcd for [M]þ 186.0656; found: 186.0656.
CDCl3)
d
6.94 (d, 2H, J¼8.0 Hz), 6.81 (d, 1H, J¼8.0 Hz), 5.98 (s, 2H),
5.87 (d, 1H, J¼1.0 Hz), 5.67 (q, 1H, J¼1.5 Hz). 13C NMR (125 MHz,
4.2.10. Methyl3-(1,1,1-trifluoroprop-2-en-2-yl)benzoate(3j). Colorless
CDCl3)
d
148.3, 147.9, 138.5 (q, J¼29.9 Hz), 127.5, 123.3 (q,
oil. Rf¼0.7 (petroleum ether); 1H NMR (500 MHz, CDCl3)
d
8.13 (s,1H),
J¼272.2 Hz), 121.5, 119.6 (q, J¼11.4 Hz), 108.3, 107.9, 101.3. 19F NMR
8.06 (d,1H, J¼3.0 Hz), 7.64 (d,1H, J¼8.0 Hz), 7.74 (t,1H, J¼8.0 Hz), 6.02
(470.0 MHz)
d
ꢁ64.8 (s, 3F).
(d, 1H, J¼1.0 Hz), 5.83 (q, 1H, J¼1.5 Hz). 13C NMR (125 MHz, CDCl3)
IR (KBr): 1509, 1449, 1366, 1233, 1120, 1044, 955, 865 cmꢁ1
HRMS (ESI): calcd for [M]þ 216.0398; found: 216.0391.
.
d
166.4, 138.2 (q, J¼30.2 Hz), 133.9, 131.6, 130.7, 130.0, 128.72, 128.70,