SPECIAL TOPIC
Reduction of Conjugated Nitroalkenes
MS: m/z (%) = 141, 94 (100), 83, 65, 55.
2563
MS: m/z (%) = 167, 120 (100), 103, 91, 77, 65, 51.
6j
6p
Colorless oil.
Colorless oil; ratio 6p/5p = 4:5.
IR (film): 3505, 2941, 1613, 1551, 1517, 1453, 1433, 1033 cm–1.
IR (film): 2802, 2669, 1713, 1468, 1431, 1268, 1243, 1223, 1194,
1160 cm–1.
13C NMR (100 MHz, CDCl3): d = 23.8, 24.6, 30.8, 84.6.
1H NMR (400 MHz, CDCl3): d = 3.17 (t, J = 7.31 Hz, 2 H), 3.80 (s,
3 H), 4.50 (t, J = 7.31 Hz, 2 H), 5.52 (br, 1 H, OH), 6.62 (m, 2 H),
6.78 (d, J = 7.96 Hz, 1 H).
13C NMR (100 MHz, CDCl3): d = 33.3, 55.9, 76.7, 111.1, 114.8,
121.3, 127.4, 145.0, 146.7.
MS: m/z (%) = 84, 83, 81, 77, 67, 65, 55 (100).
6q
Colorless oil.
IR (film): 2926, 2854, 1554, 1449, 1385 cm–1.
HRMS: m/z calcd for C9H11NO4: 197.06826; found: 197.06995.
6k
1H NMR (400 MHz, CDCl3): d = 0.84–0.93 (m, 2 H), 1.06–1.18 (m,
4 H), 1.57–1.66 (m, 5 H), 1.84 (q, J = 7.11 Hz, 2 H), 4.34 (t,
J = 7.30 Hz, 2 H).
Colorless oil.
IR (film): 3084, 2920, 1437, 1380, 1088, 1025, 779 cm–1.
1H NMR (400 MHz, CDCl3): d = 3.59–3.63 (m, 2 H), 4.47–4.51 (m,
2 H), 7.08–7.13 (t, J = 8.04 Hz, 2 H), 7.25–7.27 (d, J = 8.04 Hz,
2 H).
13C NMR (100 MHz, CDCl3): d = 25.9, 26.2, 32.7, 34.6, 34.9, 73.8.
MS: m/z (%) = 138, 122, 111, 109, 99, 94, 81, 79, 67, 55 (100).
13C NMR (100 MHz, CDCl3): d = 29.0, 72.0, 128.6, 129.4, 131.4,
135.8.
6r
Colorless oil.
HRMS: m/z calcd for C8H7Cl2NO2: 218.98483; found: 218.98395.
IR (film): 2964, 2875, 1785, 1555, 1470, 1382, 1279, 1135 cm–1.
1H NMR (400 MHz, CDCl3): d = 0.89 (d, J = 6.63 Hz, 6 H), 1.58–
1.66 (m, 1 H), 1.85 (q, J = 7.27 Hz, 2 H), 4.34 (t, J = 7.39 Hz, 2 H).
13C NMR (100 MHz, CDCl3): d = 22.0, 25.6, 36.0, 74.3.
6l
Colorless oil.
IR (film): 2977, 2929, 1557, 1279, 865, 772, 566 cm–1.
1H NMR (400 MHz, CDCl3): d = 3.17 (t, J = 7.19 Hz, 2 H), 4.52 (t,
J = 7.19 Hz, 2 H), 6.96 (m, 1 H), 7.22 (m, 1 H), 7.28 (m, 1 H).
MS: m/z (%) = 71, 69, 67, 62, 59, 55 (100).
13C NMR (100 MHz, CDCl3): d = 32.2, 75.5, 123.0, 128.0, 130.5,
130.8, 135.9.
Acknowledgment
Generous financial support by the Deutsche Forschungsgemein-
schaft (SPP 1179) and the DAAD (Scholarship to Z.G. Zhang) are
gratefully acknowledged. We thank Adelina Nemirowski and Dr.
Wolfgang Wende for help with the preparation of Figure 1.
HRMS: m/z calcd for C8H7Cl2NO2: 218.98483; found: 218.98395.
6m
Yellow solid.
IR (KBr): 3345, 3038, 2936, 1664, 1590, 1516, 1380, 1349, 1010,
808 cm–1.
References
1H NMR (400 MHz, CDCl3): d = 3.13 (t, J = 7.32 Hz, 2 H), 3.77 (s,
3 H), 4.43 (t, J = 7.32 Hz, 2 H), 5.04 (s, 2 H), 6.66 (m, 2 H), 6.75–
6.77 (d, J = 8.00 Hz, 1 H), 7.17–7.35 (m, 5 H).
13C NMR (100 MHz, CDCl3): d = 32.9, 56.0, 71.2, 76.4, 112.1,
114.6, 121.4, 127.4, 127.9, 128.1, 128.5, 136.7, 148.2, 149.0.
(1) (a) Petrus, L.; Petrusova, M.; Pham-Huu, D. P.; Lattova, E.;
Pribulova, B.; Turjan, J. Monatsh. Chem. 2002, 133, 383.
(b) Ono, N. The Nitro Group in Organic Synthesis; Wiley-
VCH: New York, 2001.
(2) (a) Ballini, R.; Petrini, M. Tetrahedron 2004, 60, 1017.
(b) Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org.
Chem. 2002, 1877.
HRMS: m/z calcd for C16H17NO4: 287.11521; found: 287.11575.
(3) Kabalka, G. W.; Guindi, L. H. M. Tetrahedron 1990, 46,
7443.
6n
(4) (a) Lee, S. H.; Park, Y. J.; Yoon, C. M. Org. Biomol. Chem.
2003, 1, 1099. (b) Kabalka, G. W.; Gai, Y. Z.; Goudgaon, N.
M.; Vacek, R. S.; Gooch, E. E. Organometallics 1988, 7,
493. (c) Varma, R. S.; Kabalka, G. W. Chem. Lett. 1985,
243. (d) Varma, R. S.; Varma, M.; Kabalka, G. W.
Tetrahedron Lett. 1985, 26, 6013. (e) Varma, R. S.; Varma,
M.; Kabalka, G. W. Tetrahedron Lett. 1985, 26, 3777.
(5) (a) Ptaszek, M.; Bhaumik, J.; Kim, H. J.; Taniguchi, M.;
Lindsey, J. S. Org. Process Res. Dev. 2005, 9, 651.
(b) Ranu, B. C.; Chakraborty, R. Tetrahedron 1992, 48,
5317.
Colorless oil.
IR (film): 2941, 2838, 1588, 1551, 1484, 1278, 1083, 1007, 750
cm–1.
1H NMR (400 MHz, CDCl3): d = 3.22 (t, J = 7.45 Hz, 2 H), 3.77 (s,
3 H), 3.79 (s, 3 H), 4.52 (t, J = 7.45 Hz, 2 H), 6.68 (m, 1 H), 6.78
(m, 1 H), 6.91 (t, J = 7.98 Hz, 1 H).
13C NMR (100 MHz, CDCl3): d = 28.7, 55.7, 60.7, 75.2, 110.0,
119.3, 124.3, 129.2, 147.3, 152.7.
HRMS: m/z calcd for C10H13NO4: 211.08391; found: 211.08459.
(6) Ranu, B. C. Synlett 1993, 885.
6o
(7) (a) Xue, D.; Chen, Y. C.; Cui, X.; Wang, Q. W.; Zhu, J.;
Deng, J. G. J. Org. Chem. 2005, 70, 3584. (b) Czekelius,
C.; Carreira, E. M. Org. Lett. 2004, 6, 4575. (c) Czekelius,
C.; Carreira, E. M. Angew. Chem. Int. Ed. 2003, 42, 4793.
(d) Arstad, E.; Barrett, A. G. M.; Tedeschi, L. Tetrahedron
Lett. 2003, 44, 2703.
Yellow oil.
IR (film): 2921, 1724, 1555, 1507, 1378, 1281, 1145, 741 cm–1.
13C NMR (100 MHz, CDCl3): d = 26.0, 73.4, 107.4, 110.1, 143.8,
149.4.
Synthesis 2007, No. 16, 2559–2564 © Thieme Stuttgart · New York