J.-W. Huang, M. Shi / Tetrahedron Letters 44 (2003) 9343–9347
9347
atmosphere (monitored by TLC), it was quenched by
the addition of 3.0 mL of water. The reaction mixture
was extracted with CH2Cl2 (3×5 mL) and the combined
organic layers were dried over anhydrous Na2SO4. The
solvent was removed under reduced pressure and the
residue was purified by silica flash column chromato-
graphy (SiO2, eluent: petroleum ether) to give the
desired product 3b as a colorless oil (96 mg, 64%).
7. Oh, B. H.; Nakamura, I.; Saito, S.; Yamamoto, Y.
Tetrahedron Lett. 2001, 42, 6203–6205.
8. Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Y. K.;
Donskaya, N. A.; Tveritinova, E. V.; Yur’eva, N. M.;
Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069–6076.
9. Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc.
1996, 118, 10676–10677.
10. Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999,
1790–1792.
11. Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc.
2000, 122, 11015–11016.
12. Chatani, N.; Takaya, H.; Hanafusa, T. Tetrahedron Lett.
1-(4,4-Diphenylbut-3-enyl)-4-methylbenzene and 1-(4,4-
diphenylbut-3-enyl)-2-methylbenzene 3b (a mixture of o-
and p-isomers, o:p=1.5:1): 3b was obtained as a color-
less oil. Yield: 64%. IR (thin film) w 3078, 3055, 3020,
2925, 2860, 1598, 1514, 1494, 1443, 1363, 1073, 1031
1988, 29, 3979–3982.
13. The reactions of MCPs with unsaturated carbon bonds
had been extensively studied. See the following review:
Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96,
64–69.
1
cm−1. H NMR (300 MHz, CDCl3, TMS) for o-isomer:
l 2.17 (s, 3H, CH3), 2.32–2.44 (m, 2H, CH2), 2.66–2.73
(m, 2H, CH2), 6.17 (t, J=7.8 Hz, 1H, CꢀCH), 7.02–
7.33 (m, 14H, ArH); for p-isomer: l 2.29 (s, 3H, CH3),
2.32–2.44 (m, 2H, CH2), 2.66–2.73 (m, 2H, CH2), 6.11
(t, J=7.5 Hz, 1H, CꢀCH), 7.02–7.33 (m, 14H, ArH).
EI-MS (m/z) 298 (M+) (3), 193 (100), 178 (21), 165 (8),
115 (49), 105 (10), 91 (15). HRMS (EI): calcd for
C23H22 (M+), 298.1722, found: 298.1740.
14. (a) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145–2149; (b) Shi,
M.; Chen, Y.; Xu, B.; Tang, J. Tetrahedron Lett. 2002,
43, 8019–8024. On the other hand, Kilburn reported
Lewis acid mediated cascade reactions of silyl-substituted
methylenecyclopropane with ketones and aldehydes. See:
(c) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D.
Tetrahedron Lett. 2000, 41, 1615–1618; (d) Peron, G. L.
N.; Norton, D.; Kitteringham, J.; Kilburn, J. D. Tetra-
hedron Lett. 2001, 42, 347–349; (e) Patient, L.; Berry, M.
B.; Kilburn, J. D. Tetrahedron Lett. 2003, 44, 1015–1017.
15. For a review of the Friedel–Crafts reaction, see: (a) Olah,
G. A. Friedel–Crafts and Related Reactions; Wiley-Inter-
science: New York, 1965; Vols. I–IV; (b) Olah, G. A.
Friedel–Crafts Chemistry; Wiley-Interscience: New York,
1973.
16. On TLC plates, no clean spot was recognized.
17. A trace of water is required to trigger the first formation
of cation 4 by means of Lewis acid BF3 (BF3+H2O+
Me2CHꢀCH2Me3CH+BF3OH−). See: (a) Evans, A. G.;
Holden, D.; Plesch, P.; Polanyi, M.; Skinner, H. A.;
Weinberger, M. A. Nature 1946, 157, 102–103; (b) Evans,
A. G.; Meadows, G. W.; Polanyi, M.; Skinner, H. A.;
Weinberger, M. A. Nature 1946, 158, 94–95; (c) Evans,
A. G.; Polanyi, M. J. Chem. Soc. 1947, 252–266.
18. Carey, F. A.; Tremper, H. S. J. Am. Chem. Soc. 1969, 91,
2967–2972.
19. For reviews on non-classical carbocations, see: (a) Olah,
G. A.; Schleyer, P. von R. Carbonium Ions; Wiley: New
York, 1968; Vol. 1, pp. 45–47; (b) McManus, S. P.
Organic Reactive Intermediates; Academic Press: New
York and London, 1973; pp. 302–321; (c) Grossel, M. C.
Organic Reaction Mechanisms, 1977; Vol. 12, pp. 321–
362; (d) Olah, G. A.; Mo, Y. K. Carbonium Ions; Wiley:
New York, 1976; Vol. 5, pp. 2135–2162; (e) Lenoir, D.
Nachr. Chem. Tech. Lab., 1978, 26, 787–790. For an
opposite opinion, see: (f) Brown, H. C. Top. Curr. Chem.
1979, 80, 1–18; (g) Brown, H. C. Pure Appl. Chem. 1982,
54, 1783–1796.
Acknowledgements
We thank the State Key Project for Basic Research
(Project 973) (No. G2000048007), Shanghai Municipal
Committee of Science and Technology, and the
National Natural Science Foundation of China for
financial support (20025206, 203900502, and 20272069).
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