The Journal of Organic Chemistry
Article
(
1
1
(
9
C ), 137.2 (C ), 135.8 (C ), 132.6 (C ), 132.5 (CH), 132.1 (CH),
31.9 (CH), 129.9 (CH), 128.7 (CH), 128.5 (CH), 128.1 (CH),
28.1 (CH), 127.4 (CH), 126.9 (CH), 126.5 (CH), 60.5 (CH), 23.7
139.9 (C ), 135.9 (C ), 132.5 (CH), 129.1 (CH), 128.7 (CH), 128.4
q q
(CH), 128.3 (CH), 128.2 (CH), 127.2 (CH), 126.7 (CH), 59.8
q
q
q
q
(CH), 42.3 (CH ). IR (ATR): 3273, 3028, 1494, 1451, 1407, 1318,
3
−
1
CH ). IR (ATR): 3274, 1707, 1446, 1335, 1222, 1163, 1112, 1023,
1151, 974, 748, 698 cm . MS (ESI) m/z (relative intensity): 310 [M
+ Na] (100), 305 [M + NH ] (20). HR-MS (ESI) m/z calcd for
C H NO SNa [M + Na] , 310.0872; found, 310.0876. The
3
−
1
+
+
+
68, 780 cm . MS (ESI) m/z (relative intensity): 420 [M + Na]
4
100), 415 [M + NH4]+ (20). HR-MS (ESI) m/z calcd for
+
(
16
17
2
+
C H ClNO SNa [M + Na] , 420.0795; found, 420.0799.
analytical data are in accordance with those reported in the
22
20
2
65
(
E)-4-Bromo-N-(1,3-diphenylallyl)benzenesulfonamide (3af).
literature.
White solid (166 mg, 78%) (n-hexane/EtOAc = 5:1). Mp = 104−
(E)-N-(1,3-Diphenylallyl)cyclopropanesulfonamide (3ak). White
1
1
1
7
1
06 °C. H NMR (400 MHz, CDCl ) δ = 7.84 (t, J = 1.8 Hz, 1H),
solid (96 mg, 61%) (n-hexane/EtOAc = 5:1). Mp = 135−137 °C. H
3
.65 (ddd, J = 7.8, 1.8, 1.0 Hz, 1H), 7.50 (ddd, J = 8.0, 2.0, 1.0 Hz,
H), 7.33−7.07 (m, 11H), 6.40 (dd, J = 15.8, 1.3 Hz, 1H), 6.11 (dd, J
NMR (400 MHz, CDCl ) δ = 7.48−7.25 (m, 10H), 6.63 (d, J = 15.9
3
Hz, 1H), 6.39 (dd, J = 15.9, 6.5 Hz, 1H), 5.31 (t, J = 7.1 Hz, 1H),
5.17 (d, J = 7.7 Hz, 1H), 2.30−2.17 (m, 1H), 1.20−1.02 (m, 2H),
=
15.8, 6.7 Hz, 1H), 5.38 (d, J = 7.4 Hz, 1H), 5.16 (t, J = 7.1, Hz,
H). 13C{ H} NMR (100 MHz, CDCl ) δ = 142.6 (C ), 138.9 (C ),
1
0.88−0.68 (m, 2H). C{ H} NMR (100 MHz, CDCl ) δ = 140.5
13
1
1
1
1
1
3
q
q
3
35.8 (C ), 135.3 (CH), 132.5 (CH), 130.3 (CH), 130.2 (CH),
28.7 (CH), 128.5 (CH), 128.1 (CH), 128.1 (CH), 127.7 (CH),
27.0 (CH), 126.6 (CH), 125.6 (CH), 122.7 (C ), 60.0 (CH). IR
(C ), 136.1 (C ), 132.1 (CH), 129.2 (CH), 128.9 (CH), 128.7 (CH),
q
q
q
128.1 (CH), 128.1 (CH), 127.2 (CH), 126.6 (CH), 59.7 (CH), 31.8
(CH), 6.0 (CH ), 6.0 (CH ). IR (ATR): 3272, 1707, 1447, 1425,
q
2
2
−
1
−1
(ATR): 3268, 3057, 1414, 1329, 1155, 1023, 974, 748, 584, 555 cm .
1327, 1297, 1144, 968, 887, 747 cm . MS (ESI) m/z (relative
intensity): 336 [M + Na] (100), 331 [M + NH ] (20). HR-MS
(ESI) m/z calcd for C H NO SNa [M + Na] , 336.1029; found,
+
+
+
MS (ESI) m/z (relative intensity): 450 [M + Na] (30), 445 [M +
NH ] (100). HR-MS (ESI) m/z calcd for C H BrNO SNa [M +
Na] , 450.0134; found, 450.0140.
4
+
79
21 18
+
4
2
18 19
2
+
336.1031.
(
E)-N-(1,3-Diphenylallyl)-4-(trifluoromethoxy)benzenesulfon-
(E)-N-(1,3-Diphenylallyl)-2-methylpropane-2-sulfonamide (3al).
amide (3ag). White solid (145 mg, 67%) (n-hexane/EtOAc = 5:1).
White solid (105 mg, 64%) (n-hexane/EtOAc = 5:1). Mp = 159−161
1
1
Mp = 106−108 °C. H NMR (400 MHz, CDCl ) δ = 7.85−7.73 (m,
°C. H NMR (400 MHz, CDCl ) δ = 7.43−7.25 (m, 10H), 6.57 (d, J
3
3
2
1
1
1
1
1
1
H), 7.33−7.17 (m, 10H), 7.12 (d, J = 8.4 Hz, 2H), 6.44 (dd, J =
= 15.8 Hz, 1H), 6.40 (dd, J = 15.8, 6.0 Hz, 1H), 5.41−5.26 (m, 1H),
4.78 (d, J = 9.0 Hz, 1H), 1.38 (s, 9H). C{ H} NMR (100 MHz,
CDCl ) δ = 141.0 (C ), 136.2 (C ), 131.6 (CH), 130.1 (CH), 128.9
1
3
1
5.9, 1.3 Hz, 1H), 6.15 (dd, J = 15.8, 6.7 Hz, 1H), 5.65 (t, J = 7.7 Hz,
1
3
1
H), 5.22 (t, J = 6.9 Hz, 1H). C{ H} NMR (100 MHz, CDCl ) δ =
51.8 (q, J
32.5 (CH), 129.3 (CH), 128.7 (CH), 128.6 (CH), 128.1 (CH),
28.0 (CH), 127.9 (CH), 127.1 (CH), 126.5 (CH), 120.7 (CH),
20.2 (q, J
CDCl ) δ = −57.71. IR (ATR): 3274, 1493, 1333, 1258, 1215, 1158,
093, 969, 921, 745 cm . MS (ESI) m/z (relative intensity): 456 [M
Na] (100), 451 [M + NH ] (70). HR-MS (ESI) m/z calcd for
3
3
q
q
3
= 1.9 Hz, C ), 139.2 (C ), 139.0 (C ), 135.8 (C ),
(CH), 128.6 (CH), 128.0 (CH), 127.8 (CH), 127.1 (CH), 126.7
C−F
q
q
q
q
(CH), 60.0 (CH), 60.0 (C ), 24.2 (CH). IR (ATR): 3272, 2981,
q
−
1
1494, 1450, 1304, 1127, 1055, 970, 934, 747 cm . MS (ESI) m/z
(relative intensity): 352 [M + Na] (100), 347 [M + NH ] (40).
HR-MS (ESI) m/z calcd for C H NO SNa [M + Na] , 352.1342;
1
19
+
+
= 259.2 Hz, C ), 60.1 (CH). F NMR (282 MHz,
C−F
q
4
+
3
19 23
2
−
1
1
+
found, 352.1346.
+
+
4
(E)-1-(1,3-Diphenylallyl)-1,3-dihydrobenzo[c]isothiazole 2,2-Di-
+
C H F NO SNa [M + Na] , 456.0852; found, 456.0857. The
oxide (3am). White solid (117 mg, 65%) (n-hexane/EtOAc = 5:1).
2
2
18
3
3
1
analytical data are in accordance with those reported in the
Mp = 165−167 °C. H NMR (400 MHz, CDCl ) δ = 7.82 (d, 1H),
3
65
literature.
E)-N-(1,3-Diphenylallyl)-4-(trifluoromethyl)benzenesulfonamide
3ah). White solid (121 mg, 58%) (n-hexane/EtOAc = 5:1). Mp =
7.60−7.48 (m, 4H), 7.46−7.38 (m, 4H), 7.37−7.28 (m, 4H), 7.30−
7.21 (m, 1H), 6.81 (d, J = 16.3 Hz, 1H), 6.59 (dd, J = 15.8, 7.1 Hz,
1H), 5.57 (d, J = 7.1 Hz, 1H), 4.35 (d, J = 13.9, Hz, 1H), 4.13 (d, J =
(
(
1
13
1
1
2
4
25−127 °C. H NMR (400 MHz, CDCl ) δ = 7.81 (d, J = 8.1 Hz,
14.0, Hz, 1H). C{ H} NMR (100 MHz, CDCl ) δ = 138.2 (C ),
3
3 q
H), 7.54 (d, J = 8.2 Hz, 2H), 7.26−7.20 (m, 6H), 7.17−7.11 (m,
H), 6.37 (d, J = 15.8 Hz, 1H), 6.10−6.01 (m, 1H), 5.19 (d, J = 3.1
136.2 (C ), 135.5 (C ), 134.1 (CH), 133.5 (C ), 132.5 (CH), 129.1
q q q
(CH), 128.9 (CH), 128.6 (CH), 128.3 (CH), 128.2 (CH), 128.1
(CH), 126.8 (CH), 126.1 (CH), 124.4 (CH), 121.3 (CH), 60.3
13
1
Hz, 2H). C{ H} NMR (100 MHz, CDCl ) δ = 144.3 (C ), 138.8
3
q
2
(
(
(
1
C ), 135.6 (C ), 134.0 (q, J
= 32.9 Hz, C ), 132.8 (CH), 128.8
(CH), 47.8 (CH ). IR (ATR): 3068, 3026, 1600, 1493, 1450, 1372,
q
q
C−F
q
2
−
1
CH), 128.6 (CH), 128.2 (CH), 128.1 (CH), 127.7 (CH), 127.5
CH), 127.0 (CH), 126.4 (CH), 125.84 (q, J
23.12 (q, J
CDCl ) δ = −63.2. IR (ATR): 3273, 1452, 1404, 1321, 1165, 1130,
062, 1018, 969, 841 cm . MS (ESI) m/z (relative intensity): 440
M + Na] (100), 435 [M + NH ] (20). HR-MS (ESI) m/z calcd for
1284, 1195, 751, 720 cm . MS (ESI) m/z (relative intensity): 384
[M + Na] (100), 379 [M + NH ] (20). HR-MS (ESI) m/z calcd for
C H NO SNa [M + Na] , 384.1029; found, 384.1031.
3
+
+
= 3.7 Hz, CH),
C−F
4
1
19
+
= 272.9 Hz, C ), 60.1 (CH). F NMR (282 MHz,
C−F
q
22 19
2
3
(E)-N-(1,3-Diphenylallyl)-N-methylmethanesulfonamide (3an).
−
1
1
[
White solid (111 mg, 73%) (n-hexane/EtOAc = 5:1). Mp = 118−
+
+
1
4
120 °C. H NMR (400 MHz, CDCl ) δ = 7.51−7.28 (m, 10H), 6.75
3
+
C H NF O SNa [M + Na] , 440.0903; found, 440.0908.
(d, J = 15.8 Hz, 1H), 6.51 (dd, J = 15.9, 7.9 Hz, 1H), 5.81 (d, J = 7.9
Hz, 1H), 2.82 (s, 3H), 2.79 (s, 3H). C{ H} NMR (100 MHz,
2
2
18
3
2
1
3
1
(E)-N-(1,3-Diphenylallyl)thiophene-2-sulfonamide (3ai). White
solid (115 mg, 65%) (n-hexane/EtOAc = 5:1). Mp = 95−97 °C.
H NMR (400 MHz, CDCl ) δ = 7.47 (dd, J = 3.7, 1.4 Hz, 1H), 7.45
dd, J = 5.0, 1.4 Hz, 1H), 7.28−7.20 (m, 10H), 6.91 (dd, J = 5.0, 3.7
Hz, 1H), 6.43 (d, J = 15.6 Hz, 1H), 6.16 (dd, J = 15.8, 6.2 Hz, 1H),
CDCl ) δ = 138.1 (C ), 135.9 (C ), 135.3 (CH), 128.8 (CH), 128.8
3
q
q
1
3
(CH), 128.4 (CH), 128.1 (CH), 127.9 (CH), 126.7 (CH), 124.2
(CH), 62.6 (CH), 38.0 (CH ), 29.9 (CH ). IR (ATR): 3028, 1494,
(
3
3
−1
1451, 1327, 1203, 1155, 956, 795, 753, 697 cm . MS (ESI) m/z
(relative intensity): 324 [M + Na] (100), 319 [M + NH ] (15).
HR-MS (ESI) m/z calcd for C H NO SNa [M + Na] , 324.1029;
1
3
1
+
+
5
(
.22−5.14 (m, 2H). C{ H} NMR (100 MHz, CDCl ) δ = 141.7
3
4
+
C ), 139.4 (C ), 136.0 (C ), 132.6 (CH), 132.2 (CH), 131.9 (CH),
q
q
q
17 19
2
1
1
1
28.8 (CH), 128.5 (CH), 128.0 (CH), 128.0 (CH), 127.9 (CH),
27.1 (CH), 127.0 (CH), 126.5 (CH), 59.9 (CH). IR (ATR): 3274,
found, 324.1030.
(E)-N-Allyl-N-(1,3-diphenylallyl)methanesulfonamide (3ao).
−
1
495, 1446, 1404, 1330, 1155, 1094, 1018, 968, 749 cm . MS (ESI)
White solid (78 mg, 40%) (n-hexane/EtOAc = 5:1). Mp = 71−78
+
+
1
m/z (relative intensity): 378 [M + Na] (100), 373 [M + NH ]
°C. H NMR (400 MHz, CDCl ) δ = 7.53 (d, J = 7.5 Hz, 2H), 7.45
4
3
+
(
40). HR-MS (ESI) m/z calcd for C H NO S Na [M + Na] ,
(d, J = 7.1 Hz, 4H), 7.41−7.32 (m, 4H), 7.29−7.17 (m, 2H), 6.97 (d,
J = 7.2 Hz, 2H), 6.70 (d, J = 15.9 Hz, 1H), 6.56 (dd, J = 15.9, 7.7 Hz,
1H), 5.80 (d, J = 7.6 Hz, 1H), 3.50−3.30 (m, 2H), 2.97−2.87 (m,
1
9
17
2 2
3
78.0593; found, 378.0599. The analytical data are in accordance with
65
those reported in the literature.
1
3
1
(
E)-N-(1,3-Diphenylallyl)methanesulfonamide (3aj). White solid
1H), 2.86 (s, 3H), 2.40 (ddd, J = 12.7, 11.0, 5.3 Hz, 1H). C{ H}
NMR (100 MHz, CDCl ) δ = 138.8 (C ), 138.6 (C ), 135.9 (C ),
1
(
(
1
100 mg, 70%) (n-hexane/EtOAc = 5:1). Mp = 86−88 °C. H NMR
3
q
q
q
400 MHz, CDCl ) δ = 7.45−7.26 (m, 10H), 6.65 (d, J = 15.8 Hz,
134.5 (CH), 128.8 (CH), 128.8 (CH), 128.8 (CH), 128.5 (CH),
128.4 (CH), 128.4 (CH), 128.3 (CH), 126.6 (CH), 126.5 (CH),
125.1 (CH), 63.3 (CH), 47.7 (CH ), 39.8 (CH), 37.5 (CH ). IR
3
H), 6.36 (dd, J = 15.8, 6.8 Hz, 1H), 5.32 (t, J = 7.0 Hz, 1H), 5.03 (d,
1
3
1
J = 7.1 Hz, 1H), 2.81 (s, 3H). C{ H} NMR (100 MHz, CDCl ) δ =
3
2
2
G
J. Org. Chem. XXXX, XXX, XXX−XXX