204
H. Takechi, H. Takahashi, and M. Machida
Vol. 42
Table 3
NMR Spectral Data for the Photoproducts 6,7,9,10 and 12
1
13
Compd.
H-NMR (CDCl , 90 MHz) δ
C-NMR (CDCl , 90 MHz) δ
3
3
6a
1.78 (6H, s, CH x2), 2.6-2.9 (2H, m, NCH CH -),
26.7(t), 33.5(q)x2, 48.2(s), 54.2(t), 110.3(d),
122.4(s), 123.7(d), 126.7(d)x2, 129.8(d),
137.8(s), 140.5(s), 198.4(s)
16.1(q), 32.6(q)x2, 34.1(t), 48.0(s), 52.3(t),
124.6(s), 124.7(s), 125.0(d), 126.3(d),
126.5(d), 128.9(d), 131.3(s), 141.4(s),
196.6(s)
32.2(q)x2, 33.0(t), 48.4(s), 52.3(t),
124.2(s), 125.7(d), 126.0(d), 127.2(s),
128.4(d)x2, 129.1(d)x2, 129.6(d), 131.8(s),
136.0(s), 142.1(s), 198.2(s)
22.0(t), 23.1(t), 29.8(q)x2, 48.4(s),
49.4(t),109.7(d), 123.5(d), 123.9(d),
126.8(d), 128.6(d), 129.5(s), 135.8(s),
139.1(s), 204.6(s)
20.8(q), 22.3(t), 28.1(q)x2, 30.2(t),
48.8(s), 49.8(t), 122.0(s), 123.8(d),
125.9(d), 127.5(d), 128.2(d), 130.5(s),
131.9(s), 141.8(s), 202.9(s)
22.7(t), 28.3(q)x2, 30.8(t), 48.8(s),
50.2(t), 123.4(d), 125.4(d)x2, 125.5(s),
127.5(d), 128.0(d), 128.7(d)x2,
128.8(d), 129.1(d), 130.6(s), 133.0(s),
141.0(s), 141.5(s), 204.2(s)
3
2
2
4.3-4.5 (2H, m, NCH CH -), 6.04 (1H, t, J=3 Hz,
2
2
CH=C-), 7.2-7.7 (4H, m, ArH)
1.74 (6H, s, CH x2), 2.23 (3H, br s, CH ),
6b
6c
7a
7b
7c
3
3
2.6-2.9 (2H, m, NCH CH -), 4.2-4.4 (2H, m,
2
2
NCH CH -), 7.1-7.6 (3H, m, ArH), 7.6-7.8
2
2
(1H, m, ArH)
1.78 (6H, s, CH x2), 3.07 (2H, br t,J= 8 Hz,
3
NCH CH -), 4.45 (2H, br t, J= 8 Hz, NCH -),
2
2
2
6.8-7.0 (1H, m, ArH), 7.1-7.6 (8H, m, ArH)
1.66 (6H, s, CH x2), 1.8-2.1 (2H, m, NCH CH -),
3
2
2
2.2-2.5 (2H, m, C=C-CH -), 4.4-4.6 (2H, m,
2
NCH CH -), 5.93 (1H, t, J= 4 Hz, CH=C-),
2
2
7.1-7.6 (4H, m, ArH)
1.63 (6H, s, CH x2), 1.8-2.1 (2H, m, NCH CH -),
3
2
2
2.12 (3H, s, CH ), 2.1-2.4 (2H, m, C=C-CH -),
3
2
4.38 (2H, m, br t, J= 6 Hz, NCH CH -),
2
2
7.1-7.5 (4H, m, ArH )
1.76 (6H, s, CH x2), 2.0-2.3 (2H, m, NCH CH -),
3
2
2
2.67 (2H, t, J= 6 Hz, C=C-CH -), 4.3-4.6 (2H,
2
m, NCH CH -), 6.5-6.9 (2H, m, ArH), 7.0-7.4
2
2
(7H, m, ArH)
9a[a]
10b
1.68 (3H, s, CH ), 1.94 (3H, s, CH ), 3.03
27.6(q), 32.7(q), 47.6(s), 50.2(d),
57.7(t), 80.7(s), 123.1(d), 125.0(d),
125.9(d), 126.8(d)x2, 127.6(d), 128.5(d),
128.9(d)x2, 129.2(d), 135.5(d), 136.2(s),
138.6(s), 141.0(s), 206.8(s)
27.9(t), 31.8(q)x2, 48.8(s), 52.3(t),
122.4(d), 124.9(s), 125.3(s), 125.9(d),
126.7(d), 126.9(d), 128.2(d), 128.9(d),
129.6(d), 132.8(d), 133.5(s), 137.3(s),
142.6(s), 198.2(s)
3
3
(1H, s, SH), 3.9-4.0 (1H, m, CH-CH=CH-),
4.45-4.55 (1H, m, NCH -), 4.65-4.75 (1H, m,
2
NCH -), 6.6-6.7 (2H, m CH=CH-), 7.1-7.6
2
(9H, m, ArH)
1.74 (6H, s, CH x2), 3.04 (2H, t, J= 8 Hz,
3
NCH CH -), 4.2-4.5 (2H, m, NCH -), 6.74
2
2
2
(1H, d, J= 15.4 Hz, CH=CHPh), 7.1-7.6 (9H,
m, CH=CHPh and ArH), 7.6-7.9 (1H, m, ArH)
10c
1.66 (6H, s, CH x2), 1.9-2.3 (2H, m, NCH CH -),
22.1(t), 24.3(t), 28.4(q)x2, 49.1(s),
51.0(t), 122.2(s), 124.1(d), 126.1(d),
126.6(d), 127.4(d), 127.8(d), 128.9(d),
129.7(d), 130.2(s), 135.7(s), 137.6 (s),
142.3(s), 203.7(s)
3
2
2
2.68 (2H, t, J= 6.5 Hz, C=C-CH -), 4.2-4.5
2
(2H, m, NCH -), 6.83 (1H, d, J= 16 Hz,
2
CH=CHPh), 7.1-7.6 (10H, m, CH=CHPh and ArH)
12a-i
0.6-1.0 (1H, m, CH -), 1.0-2.0 (3H, m,
21.7(q), 27.4(t), 28.7(t), 30.9(q), 34.0(t),
47.6(s), 50.2(d), 72.2(s), 123.7(d),
125.2(d), 127.2(d), 128.9(d), 136.9(s),
139.3(s), 175.7(s)
2
CH CH CH-), 1.62 (3H, s, CH ), 2.67 (1H,
2
2
3
dd, J= 10, 8 Hz, SCH CH-), 2.88 (1H, t,
2
J= 8 Hz, SCH CH-), 3.12 (3H, s, NCH ),
2
3
3.1-3.5 (1H, m, SCH CH-), 7.3-7.6 (3H,
2
m, ArH), 8.1-8.3 (1H, m, ArH)
12a-ii 1.2-2.0 (4H, m, CH CH CH-), 1.68 (3H, s,
22.3(q), 28.6(t), 30.4(t), 32.6(q), 34.6(t),
47.3(s), 50.9(d), 74.8(s), 122.5(d),
123.5(d), 126.6(d), 127.8(d), 141.5(s),
143.3(s), 174.2(s)
26.0(t), 26.3(q), 26.7(t), 29.4(t), 32.1(q),
46.9(s), 47.1(t), 59.9(d), 76.3(s), 125.1(d),
126.9(d), 127.3(d), 129.3(d), 133.7(s),
143.0(s), 174.6(s),
2
2
CH ), 2.6-3.1 (2H, m, SCH CH-), 3.0-3.5(1H,
3
2
m, SCH CH-), 3.58 (3H, s, NCH ), 7.1-7.5 (4H,
2
3
m, ArH)
0.4-0.8 (1H, m, CH -), 0.8-1.8 (4H, m, CH CH -),
12b-i
2
2
2
1.70 (3H, s, CH ), 2.0-2.3 (1H, m, CH -),
3
2
2.5-2.9 (2H, m, SCH CH-), 3.42 (3H, s, NCH ),
2
3
3.3-3.8 (1H, m, SCH CH-), 7.3-7.6 (3H, m,
2
ArH), 8.2-8.5 (1H, m, ArH)
12b-ii 0.4-1.0 (1H, m, CH -), 1.2-2.4 (5H, m,
25.7(q), 25.7(t), 27.4(t), 30.0(t), 33.9(q),
46.3(s), 47.1(t), 64.4(d), 78.1(s), 125.3(d),
125.7(d), 127.2(d), 128.3(d), 137.3(s),
140.2(s), 176.7(s)
2
CH CH CH -), 1.66 (3H, s, CH ), 2.6-3.1 (2H,
2
2
2
3
m, SCH CH-), 3.2-3.6(1H, m, SCH CH-),
2
2
3.79 (3H, s, NCH ), 7.3-7.5 (3H, m, ArH),
3
7.9-8.1 (1H, m, ArH)
[a] NMR spectra were acquired on JEOL JNM-ECA 500 spectrometer.