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PAPER
Table 4 Spectroscopic Data for 3-Alkyl Succinic Anhydrides 6a–k
Product IR (film)
(cm–1)
1H NMR (CDCl3) (ppm), J (Hz)
13C NMR (75 MHz, CDCl3) (ppm) MS: m/z
6a
6b
6c
6d
6e
6f
1861, 1784 0.91 (d, 3 H, J = 6.4), 0.95 (d, 3 H, J = 6.4), 1.43– 174.07, 170.18, 40.10, 39.21, 34.58, 157 [M+], 141, 113, 100,
1.54 (m, 1 H), 1.62–1.76 (m, 1 H), 1.77–1.87 (m, 26.10, 22.68, 21.43
1 H), 2.56–2.68 (m, 1 H), 2.98–3.18 (m, 2 H)
84, 56 (100), 43
1860, 1781, 1.56–1.78 (m, 3 H), 1.8–1.97 (m, 1 H), 2.18 (s, 208.09, 173.68, 170.13, 42.71,
184 [M+], 166, 156, 141,
112, 58, 43 (100)
1712
3 H), 2.4–2.57 (m, 2 H), 2.61–2.84 (m, 1 H),
3.01–3.22 (m, 2 H)
40.82, 34.17, 30.40, 30.20, 20.77
1860, 1780 0.91 (d, 6 H, J = 6.6), 1.14–1.42 (m, 2 H), 1.48– 173.65, 170.12, 40.77, 35.62, 34.00, 169, 155, 137, 100, 83,
1.74 (m, 2 H), 1.86–2.05 (m, 1 H), 2.58–2.76 (m, 28.83, 27.73, 22.32, 22.20
1 H), 3.0–3.18 (m, 2 H)
70, 56 (100), 41, 29
1866, 1790 0.95 (t, 3 H, J = 7.3), 1.34–1.48 (m, 2 H), 1.54– 173.67, 170.12, 40.45, 34.08, 32.99, 114, 100, 70 (100), 55,
1.68 (m, 1 H), 1.83–1.97 (m, 1 H), 2.57–2.7 (m, 20.02, 13.54
1 H), 2.98–3.14 (m, 2 H)
42, 29
1861, 1783, 1.22–1.41 (m, 6 H), 1.43–1.71 (m, 2 H), 2.02 (s, 177.52, 173.61, 170.05, 64.32,
224, 199, 181, 164, 43
(100)
1732
3 H), 2.4–2.83 (m, 2 H), 3.01–3.16 (m, 1 H), 4.0 40.61, 34.09, 30.85, 28.69, 28.44,
(t, 2 H, J = 6.6) 26.58, 25.59, 20.97
1862, 1782 0.9 (t, 3 H, J = 6.4), 1.24– 1.48 (m, 6 H), 1.55– 173.61, 170.05, 40.67, 34.08, 31.21, 152, 142, 100, 98, 83, 70,
1.75 (m, 1 H), 1.85–2.04 (m, 1 H), 2.58–2.76 (m, 30.96, 26.36, 22.32, 13.91
1 H), 3.0–3.18 (m, 2 H)
56 (100), 55, 41, 29, 27
6g
6h
6i
1864, 1778, 1.87–2.0 (m, 1H), 2.24–2.37 (m, 1H), 2.54–2.88 173.66, 170.02, 139.53, 128.81,
204 [M+], 186, 132, 105,
1603
(m, 3 H), 2.96–3.1 (m, 2 H)
128.28, 126.70, 39.76, 34.16, 32.90, 104 (100), 100, 91, 77,
32.53 55, 39
1859, 1780 0.96–1.32 (m, 6 H), 1.48–1.58 (m, 1 H), 1.60–
173.42, 170.99, 46.81, 39.42, 31.70, 182 [M+], 164, 137, 110,
1.80 (m, 3 H), 1.80–1.93 (m, 1 H), 2.70 (dd, 1 H, 30.63, 28.81, 26.37, 26.19
J = 4.9, 18), 2.86–3.06 (m, 2 H)
100 (100), 81, 67, 55, 41,
27
1860, 1780 0.87 (t, 3 H, J = 6.7), 1.16–1.44 (br s, 18 H),
1.54–1.70 (m, 1 H), 1.84–1.98 (m, 1 H), 2.58–
2.72 (m, 1 H), 3.02–3.16 (m, 2 H)
173.65, 170.10, 40.67, 34.08, 31.90, 254 [M+], 236, 182, 156,
30.99, 29.58, 29.47, 29.32, 29.78,
29.07, 26.70, 22.68, 14.12
142, 111, 97 (100), 83,
69, 43, 41, 29
6j
1861, 1782 0.94 (d, 1.8 H, J = 6.9), 1.03 (d, 1.2 H, J = 6.6), 207.85, 207.64, 173.15, 172.54,
170, 152, 141, 127, 58,
1.4–1.8 (m, 3 H), 2.15 (s, 1.8 H), 2.17 (s, 1.2 H), 170.14, 170.04, 45.87, 45.49, 40.86, 43 (100),
2.46–2.58 (m, 2 H), 2.7–3.22 (m, 3 H)
33.78, 33.06, 31.81, 31.74, 30.02,
29.93, 29.75, 27.50, 26.75, 16.38,
14.86
6k
1842, 1764, 2.73 (dd, 1 H, J = 6.6, 19.0), 2.89–3.12 (m, 2 H), 173.3, 170.02, 136.02, 129.17,
1600 3.26 (dd, 1 H, J = 5.0, 14.1), 3.38–3.56 (m, 1 H), 128.94, 127.63, 42.14, 36.02, 32.96, 117, 91 (100), 77, 51, 39
7.10–7.48 (m, 5 H)
190 [M+], 172, 162, 148,
Table 5 Spectroscopic Data for 2-Alkylidene Succinic Acids 7a–e
Product
7a
IR (film)
(cm–1)
1H NMR (CDCl3) (ppm), J (Hz)
13C NMR (75 MHz, CDCl3) (ppm)
1828, 1694, 1.09 (d, 6 H, J = 6.9), 2.56–2.77 (m, 1 H), 3.52 (s, 2 H,), 172.00, 168.26, 150.07, 124.48, 32.04, 27.53, 21.78
1652
6.88 (d, 1 H, J = 10.2)
7b
1713
2.04 (s, 3 H), 2.37–2.49 (m, 2 H), 2.6 (t, 2 H, J = 6.9), 3.38 207.38, 176.06, 171.59, 146.45, 125.63, 31.86, 29.89,
(s, 2 H), 6.98 (t, 1 H, J = 7.6)
23.09, 20.83
7c
1710
0.92 (d, 6 H, J = 6.7), 1.68–1.87 (m, 1 H), 2.01 (dd, 2 H, 176.93, 172.18, 147.82, 125.13, 38.09, 32.16, 29.70,
J = 7.0, 7.6), 3.38 (s, 2 H), 7.12 (t, 1 H, J = 7.6)
28.22, 22.45
7d
1708, 1676 1.0 (t, 3 H, J = 7.6), 2.18 (q, 2 H, J = 7.5), 3.2 (s, 2 H),
6.98 (t, 1 H, J = 7.5), 12.28 (br s, 2 H)
171.94, 168.06, 145.39, 126.09, 31.83, 21.52, 12.91
7e
3344, 1714 1.2–1.47 (m, 6 H), 2.08–2.22 (m, 2 H), 3.18 (s, 2 H), 3.36 171.93, 168.01, 144.01, 126.60, 60.52, 32.25, 28.13,
(t, 2 H, J = 6.4), 6.8 (t, 1H, J = 7.5), 12.2 (br s, 2 H) 27.90, 25.16, 20.99
Synthesis 2002, No. 5, 681–685 ISSN 0039-7881 © Thieme Stuttgart · New York