J. Streuff, K. Mun˜iz / Journal of Organometallic Chemistry 690 (2005) 5973–5978
5977
126.85, 127.24, 128.29, 132.74, 138.88, 163.67. MS (EI, eV):
2.1.10. Fumaric amide 4f
m/z (%): 294.2 [M]+, 189.1 (5), 160.1 (7), 117.1 (4), 106.1
(100), 91.1 (36), 65.1 (3). HRMS: calc.: 294.1368, found:
294.1375. IR (KBr): m (cmꢀ1) = 3282, 3086, 3032, 2970,
2927, 1630, 1564, 1454, 1433, 1338, 1261, 1242, 1192,
1082, 1036, 987, 800, 714, 694.
Prepared by the general procedure. [a]D = +34
(c = 0.14 g/100 mL, DMSO). 1H NMR (300 MHz,
DMSO): d (ppm) = 1.51 (d, J = 7.0 Hz, 6H), 5.77 (quin,
J = 7.2 Hz, 2H), 6.92 (s, 2H), 7.47–7.57 (m, 8H), 7.81
(dd, J = 1.3, 7.5 Hz, 2H), 7.93 (dd, J = 1.9, 7.5 Hz, 2H),
8.10 (dd, J = 1.3, 7.9 Hz, 2H), 8.97 (d, J = 8.10 Hz, 2H).
13C NMR (75 MHz, DMSO-d6): d (ppm) = 21.42, 44.31,
122.26, 122.94, 125.39, 126.14, 127.28, 128.59, 130.22,
132.81, 133.31, 139.67, 162.63. MS (EI, eV): m/z (%):
422.2 (8) [M]+, 171.1 (15), 170.1 (100), 155.0 (50), 129.0
(5). HRMS: calc.: 422,1994, found: 422.2005. IR (KBr): m
(cmꢀ1) = 3278, 3070, 3060, 2972, 2931, 2873, 1621, 1541,
1452, 1348, 1192, 1119, 1005, 798, 775.
2.1.6. Fumaric amide 4b: [21]
Prepared using the general procedure. 1H NMR
(300 MHz, Methanol-d4): d (ppm) = 0.89 (t, J = 7.0 Hz,
6H), 1.32 (m, 20H), 1.54 (m, 4H), 4.51 (m, 4H), 6.85 (s,
2H), 7.87 (s, 2NH). MS (EI, eV): m/z (%): 338.2 [M]+,
309.2 (3), 295.2 (3), 281.2 (10), 267.1 (20), 253.1 (6), 239.1
(8), 227.1 (8), 211.1 (100), 184.1 (4), 182.1 (12), 168.1 (4),
140.1 (3), 129.1 (6), 128.1 (64), 112.0 (3), 98.0 (10), 71.1
(4), 57.1 (6). HRMS: calc.: 338.2933, found: 338,2937. IR
(KBr): m (cmꢀ1) = 3294, 3066, 2958, 2924, 2873, 2852,
1622, 1551, 1470, 1329, 1192, 999, 673.
2.1.11. Fumaric amide 4g: [10b]
Prepared by the general procedure. 1H NMR (300 MHz,
DMSO):d(ppm) = 1.28(s, 18H), 6.78(s, 2H), 7.97(brs, 2H).
2.1.7. Fumaric amide 4c
Acknowledgements
Prepared using the general procedure. 1H NMR
(300 MHz, DMSO-d6): d (ppm) = 1.10–1.77 (m, 20H),
3.59 (m, 2H), 6.79 (s, 2H), 8.19 (d, J = 7.34 Hz, 2H). MS
(EI, eV): m/z (%): 278.1 [M]+, 197.1 (100), 180.0 (12),
152.0 (8), 115.0 (32), 98.0 (49), 83.0 (8), 67.0 (3), 56.0
(10). HRMS: calc.: 278.1994, found: 278.1990. IR (KBr):
m (cmꢀ1) = 3284, 3076, 2931, 2856, 1632, 1545, 1455,
1344, 1194, 1096, 1003.
This work was generously supported by the Deutsche
Forschungsgemeinschaft (MU-1811-1/1) and the Fonds
der Chemischen Industrie. J.S. is grateful to Bonn Univer-
sity for a Theodor–Laymann-fellowship. The authors are
grateful to Prof. Dr. K.H. Do¨tz for his ongoing support
and interest.
References
2.1.8. Fumaric amide 4d
Prepared using the general procedure. 1H NMR
(300 MHz, DMSO-d6): d (ppm) = 1.57 (s, 12H), 6.86 (s,
2H), 7.16-7.32 (m, 10H), 8.53 (s, 2 NH). 13C NMR
(75 MHz, DMSO-d6): d (ppm) = 29.24, 55.06, 124.61,
125.78, 127.85, 133.31, 147.31, 162.85. MS (EI, eV): m/z
(%): 350.1 [M]+, 335.1 (8), 293.1 (3), 232.1 (5), 231.1 (6),
215.1 (10), 200.0 (2), 188.1 (3), 175.0 (6), 160.0 (8), 134.1
(8), 120.1 (100), 98.0 (6), 91.0 (22), 79.0 (4), 58.1 (5).
HRMS: calc.: 350.1994, found: 350.1986. IR (KBr): m
(cmꢀ1) = 3300, 3062, 3026, 3003, 2981, 2943, 2877, 1645,
1551, 1495, 1446, 1385, 1336, 1254, 1207, 1171, 1105,
1032, 987, 759, 694, 669.
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2.1.9. Fumaric amide 4e: [22]
Prepared by the general procedure. [a]D = ꢀ140
(c = 0.10 g/100 mL, methanol). 1H NMR (300 MHz,
DMSO-d6): d (ppm) = 1.36 (d, J = 7.0 Hz, 6H), 4.98 (pseu-
do quin, J = 7.0 Hz, 2H), 6.88 (s, 2H), 7.28–7.30 (m, 10H),
8.13 (d, J = 8,34 Hz, 2NH). 13C NMR (75 MHz, DMSO-
d6): d (ppm) = 22.37, 48.17, 125.91, 126.74, 128.31,
132.88, 144.23, 162.85. MS (EI, eV): m/z (%): 322.2 [M]+,
307.2 (20), 279.2 (1), 203.1 (2), 174.1 (1), 160.1 (0), 149.1
(2), 131.1 (3), 120.1 (100), 105.1 (44), 99.0 (10), 91.1 (2),
77.1 (4), 55.1 (2). HRMS calc.: 322.1681, found:
322.1689. IR (KBr): m (cmꢀ1) = 3278, 3066, 2968, 2929,
1632, 1549, 1448, 1356, 1261, 1209, 1192, 1105, 1020,
993, 802, 696.