PAPER
Ceric(IV)-Mediated Reaction of Methylenecyclopropanes
613
4a11a
Oil.
References
(1) (a) Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589.
IR: 1781, 1492, 1078, 702 cm–1.
1H NMR (400 MHz): d = 2.83 (t, 2 H, J = 8.4 Hz), 3.15 (t, 2 H,
J = 8.4 Hz), 7.20–7.38 (m, 10 H).
13C NMR (100 MHz): d = 209.22, 142.51, 129.14, 127.33, 126.83,
76.62, 43.80, 26.02.
(b) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem.
Rev. 2003, 103, 1213. (c) Yamago, S.; Nakamura, E. Org.
React. 2002, 61, 1. (d) Nakamura, E.; Yamago, S. Acc.
Chem. Res. 2002, 35, 867. (e) Yamago, S.; Takeichi, A.;
Nakamura, E. Synthesis 1996, 1380.
(2) (a) Binger, P.; Büch, H.; M, Top. Curr. Chem. 1987, 135,
77. (b) Ohta, T.; Takaya, H. In Comprehensive Organic
Synthesis, Vol. 5; Trost, B. M., Ed.; Pergamon: Oxford,
1991, 1185. (c) Suginome, M.; Matsuda, T.; Ito, Y. J. Am.
Chem. Soc. 2000, 122, 11015. (d) Nakamura, I.; Saito, S.;
Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (e) Oh,
B. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron
Lett. 2001, 42, 6203. (f) Camacho, D. H.; Nakamura, I.;
Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270.
(g) Nakamura, I.; Oh, B. H.; Saito, S.; Yamamoto, Y.
Angew. Chem. Int. Ed. 2001, 40, 1298. (h) Nakamura, I.;
Siriwardana, A. I.; Saito, S.; Yamamoto, Y. J. Org. Chem.
2002, 67, 3445. (i) Camacho, D. H.; Nakamura, I.; Oh, B.
H.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2002, 43,
2903. (j) Siriwardana, A. I.; Nakamura, I.; Yamamoto, Y.
Tetrahedron Lett. 2003, 44, 985. (k) Xu, B.; Shi, M. Org.
Lett. 2003, 5, 1415. (l) Ma, S.; Lu, L.; Zhang, J. J. Am.
Chem. Soc. 2004, 126, 9645. (m) López, F.; Delgado, A.;
Rodriguez, J. R.; Castedo, L.; Mascareñas, J. L. J. Am.
Chem. Soc. 2004, 126, 10262. (n) Nötzel, M. W.; Tamm,
M.; Labahn, T.; Noltemeyer, M.; Es-Sayed, M.; de Meijere,
A. J. Org. Chem. 2000, 65, 3850. (o) Nötzel, M. W.;
Labahn, T.; Es-Sayed, M.; de Meijere, A. Eur. J. Org. Chem.
2001, 3025. (p) Nakamura, I.; Yamamoto, Y. Adv. Synth.
Catal. 2002, 344, 111.
MS (70 eV, EI): m/z (%) = 222 (M+, 20.14).
4b
Oil.
IR: 1780, 1509, 1492, 1077 cm–1.
1H NMR (400 MHz): d = 2.29 (s, 3 H), 2.80 (t, 2 H, J = 8.6 Hz),
3.14 (t, 2 H, J = 8.6 Hz), 7.10–7.37 (m, 9 H).
13C NMR (100 MHz): d = 209.11, 142.33, 139.23, 136.66, 129.46,
128.74, 126.88, 126.44, 126.36, 75.98, 43.40, 25.66, 21.02.
MS (70 eV, EI): m/z (%) = 236 (M+, 2.82).
Anal. Calcd for C17H16O: C, 86.40; H, 6.82. Found: C, 86.30; H,
6.85.
4h
Oil.
IR: 1782, 1490, 1077 cm–1.
1H NMR (400 MHz): d = 2.75–2.83 (m, 2 H), 3.11–3.17 (m, 2 H),
7.20–7.34 (m, 9 H).
13C NMR (100 MHz): d = 208.27, 141.65, 140.60, 132.84, 128.88,
128.85, 127.82, 127.17, 126.32, 75.54, 43.48, 25.59.
MS (70 eV, EI): m/z (%) = 256 (M+, 16.21).
(3) (a) Melikyan, G. G. Org. React. 1997, 49, 427. (b) Snider,
B. B. Chem. Rev. 1996, 96, 339. (c) Linker, T. J.
Anal. Calcd for C16H13ClO: C, 74.85; H, 5.10. Found: C, 74.68; H,
5.15.
Organomet. Chem. 2002, 661, 159. (d) Nair, V.; Mathew,
J.; Prabhakaran, J. Chem. Soc. Rev. 1997, 127.
(e) Vinogradov, M. G.; Kondorsky, A. E.; Nikishin, G. I.
Synthesis 1988, 60. (f) Lee, Y. R.; Suk, J. Y.; Kim, B. S.
Org. Lett. 2000, 2, 1387. (g) Hong, B. C.; Shen, I. C.; Liao,
J. H. Tetrahedron Lett. 2001, 42, 935.
4i
Oil.
IR: 1781, 1507 cm–1.
1H NMR (400 MHz): d = 2.76–2.84 (m, 2 H), 3.11–3.18 (m, 2 H),
6.96–7.35 (m, 9 H).
13C NMR (100 MHz): d = 208.55, 161.69 (d, JC,F = 244.0 Hz),
141.89, 137.88 (d, JC,F = 3.3 Hz), 128.82, 128.05 (d, JC,F = 8.2 Hz),
127.06, 126.33, 115.52 (d, JC,F = 21.1 Hz), 75.47, 43.42, 25.72.
(4) (a) Nair, V.; Balagopal, L.; Rajan, R.; Mathew, J. Acc.
Chem. Res. 2004, 37, 21. (b) Nair, V.; Mathew, J.;
Radhakrishnan, K. V. J. Chem. Soc., Perkin Trans. 1 1996,
1487. (c) Kajikawa, S.; Nishino, H.; Kurosawa, K.
Heterocycles 2001, 54, 171. (d) Lee, Y. R.; Kim, B. S.; Kim,
D. H. Tetrahedron 2000, 56, 8845. (e) Miura, M.; Arai, N.;
Narasaka, K. Bull. Chem. Soc. Jpn. 1998, 71, 1437. (f) Lee,
Y. R.; Byun, M. W.; Kim, B. S. Bull. Korean Chem. Soc.
1998, 19, 1080. (g) Nair, V.; Mathew, J.; Kanakamma, P. P.;
Panicker, S. B.; Sheeba, V.; Zeena, S.; Eigendorf, G. K.
Tetrahedron Lett. 1997, 38, 2191. (h) Nair, V.; Sheeba, V.;
Panicker, S. B.; George, T. G.; Rajan, R.; Balagopal, L.;
Vairamani, M.; Prabhakar, S. Tetrahedron 2000, 56, 2461.
(5) For radical reactions related to MCPs, see: (a) Mizuno, K.;
Nire, K.; Sugita, H.; Otsuji, Y. Tetrahedron Lett. 1993, 34,
6563. (b) Mizuno, K.; Maeda, H.; Sugita, H.; Nishioka, S.;
Hirai, T.; Sugimoto, A. Org. Lett. 2001, 3, 581.
MS (70 eV, EI) m/z (%) = 240 (M+, 5.15).
Anal. Calcd for C16H13FO: C, 79.98; H, 5.45. Found: C, 79.88; H,
5.51.
4j11
Oil.
IR: 1782, 1601, 1507, 1230, 832 cm–1.
1H NMR (400 MHz): d = 2.79 (t, 2 H, J = 8.4 Hz), 3.18 (t, 2 H,
J = 8.4 Hz), 6.97–7.02 (m, 4 H), 7.29–7.31 (m, 4 H).
13C NMR (100 MHz): d = 208.28, 161.74 (d, JC,F = 244.9 Hz),
137.66 (d, JC,F = 3.2 Hz), 127.98 (d, JC,F = 8.1 Hz), 115.64 (d,
JC,F = 21.8 Hz), 74.76, 43.44, 25.86.
(c) Legrand, N.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron
Lett. 2000, 41, 9815. (d) Destabel, C.; Kilburn, J. D.;
Knight, J. Tetrahedron 1994, 50, 11267. (e) Boffey, R. J.;
Santagostino, M.; Whittingham, W. G.; Kilburn, J. D. Chem.
MS (70 eV, EI): m/z (%) = 258 (M+, 15.11).
Acknowledgment
This work was supported by the National Natural Science Founda-
tion of China (20332060, 20472072).
Synthesis 2006, No. 4, 609–614 © Thieme Stuttgart · New York