K. Yu. Koltunov, G. K. S. Prakash, G. Rasul, G. A. Olah
FULL PAPER
lam, R. E. Daniels, K. N. Kudin, M. C. Strain, O. Farcas, J.
Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pom-
elly, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y.
Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K.
Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B.
Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.
Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham,
C. Y. Peng, A. Nanayakkarra, C. Gonzalez, M. Challacombe,
P. M. W. Gill, B. Jonson, W. Chen, M. W. Wong, J. L. Andres,
C. Gonzalez, M. Head-Gordon, J. A. Pople, Gaussian 98 (Re-
vision A.5), Gaussian, Inc., Pittsburgh, PA, 1998.
Method b: A mixture of AlCl3 (2.7 g, 20 mmol) and 14 (0.7 g,
3.8 mmol) in benzene (6 mL) was stirred at 90 °C for 30 h, followed
by treatment as described above to give compound 12 (0.9 g, 83%).
Supporting Information (see also the footnote on the first page of
this article): 1H and 13C NMR spectroscopic data of known as well
as newly obtained compounds 5 and 7–12.
Acknowledgments
[16] T. Ziegler, Chem. Rev. 1991, 91, 651–667.
Support of the work by the National Science Foundation and the
Loker Hydrocarbon Research Institute is gratefully acknowledged.
[17] Becke’s three-parameter hybrid method using the LYP corre-
lation functional: a) A. D. Becke, J. Chem. Phys. 1993, 98,
5648–5652; b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988,
37, 785–789; c) P. J. Stephens, F. J. Devlin, C. F. Chabalovski,
M. J. Frisch, J. Phys. Chem. 1994, 98, 11623–11627.
[18] W. J. Hehre, L. Radom, P. v. R. Schleyer, J. A. Pople, Ab initio
Molecular Orbital Theory, Wiley-Interscience, New York, 1986.
[19] A. E. Reed, L. A. Curtiss, F. Wienhold, Chem. Rev. 1988, 88,
899–926.
[20] G. A. Olah, G. K. S. Prakash, J. Sommer, Superacids, John
Wiley & Sons, New York, 1985.
[21] a) J. T. Baker, S. Sifniades, J. Org. Chem. 1979, 44, 2798–2800;
b) D. A. Lightner, Y.-T. Park, Tetrahedron 1979, 35, 463–471.
[22] K. Yu. Koltunov, I. B. Repinskaya, G. I. Borodkin, Russ. J.
Org. Chem. 2001, 37, 1534–1541.
[1] G. Rasul, G. K. S. Prakash, G. A. Olah, J. Phys. Chem. A 2006,
110, 1041–1045.
[2] a) C. H. Thomas, Anhydrous Aluminum Chloride in Organic
Chemistry, Van Nostrand Reinhold, New York, 1941; b) G. P.
Rice, J. Am. Chem. Soc. 1931, 53, 3153–3159; c) J. E. Hofmann,
A. Schriesheim, in Friedel–Crafts and Related Reactions (Ed.:
G. A. Olah), Interscience, New York, 1964, vol. II, pp. 597–
640; d) G. Drechsler, S. Smagin, J. Prakt. Chem. 1965, 28, 315–
324; e) D. A. Klumpp, K. Y. Yeung, G. K. S. Prakash, G. A.
Olah, J. Org. Chem. 1998, 63, 4481–4484, and references cited
therein.
[3] a) K. Yu. Koltunov, S. Walspurger, J. Sommer, Tetrahedron
Lett. 2004, 45, 3547–3549; b) K. Yu. Koltunov, S. Walspurger,
J. Sommer, Eur. J. Org. Chem. 2004, 19, 4039–4047; c) D. A.
Klumpp, R. Rendy, Y. Zhang, A. Gomez, A. McElrea, Org.
Lett. 2004, 6, 1789–1792.
[23] K. Yu. Koltunov, S. Walspurger, J. Sommer, Chem. Commun.
2004, 15, 1754–1755.
[24] Under these reaction conditions cyclohexane exists in an equi-
librium with methylcyclopentane, see: C. D. Nenitzescu, R.
Cantuniari, Ber. Dtsch. Chem. Ges. 1933, 66, 1097–1100.
[25] L. S. Benner, Y.-H. Lai, K. P. C. Vollhardt, J. Am. Chem. Soc.
1981, 103, 3609–3611, and references cited therein.
[26] a) I. B. Repinskaya, K. Yu. Koltunov, M. M. Shakirov, L. N.
Shchegoleva, V. A. Koptyug, Russ. J. Org. Chem. 1993, 29,
803–810; b) K. Yu. Koltunov, E. N. Subbotina, I. B. Repin-
skaya, Russ. J. Org. Chem. 1997, 33, 689–693.
[27] Complex 15, for example, is quantitatively formed in the reac-
tion of sodium phthalimide with one molar equivalent of
AlCl3: R. P. Verma, T. N. Misra, J. Indian Chem. Soc. 1976, 53,
1230–1232.
[28] For comparison with general synthetic routes to 11, see the
review: T. Ichiro, H. Minoru, Heterocycles 1997, 45, 2475–
2500.
[29] For multi-step syntheses and the biological activity of 8 and its
derivatives see, for example: a) M. J. Kornet, A. M. Crider, J.
Med. Chem. 1977, 20, 1210–1213; b) M. J. Daly, G. W. Jones,
P. J. Nicholls, H. J. Smyth, M. G. Rowlands, M. A. Bunnett, J.
Med. Chem. 1986, 29, 520–523; c) R. Whomsley, H. J. Smith,
P. J. Nicholls, W. Nazareth, M. Ahmadi, J. Enzym. Inhib. 1993,
6, 317–330.
[4] K. Yu. Koltunov, G. K. S. Prakash, G. Rasul, G. A. Olah, Tet-
rahedron 2002, 58, 5423–5426.
[5] a) K. Yu. Koltunov, I. B. Repinskaya, Russ. J. Org. Chem. 2002,
38, 437–442; b) K. Yu. Koltunov, G. K. S. Prakash, G. Rasul,
G. A. Olah, J. Org. Chem. 2002, 67, 4330–4336; c) K. Yu. Kol-
tunov, G. K. S. Prakash, G. Rasul, G. A. Olah, J. Org. Chem.
2002, 67, 8943–8951; d) K. Yu. Koltunov, G. K. S. Prakash, G.
Rasul, G. A. Olah, Heterocycles 2004, 62, 757–772.
[6] D. A. Klumpp, M. Garza, A. Jones, S. Mendoza, J. Org. Chem.
1999, 64, 6702–6705.
[7] D. A. Klumpp, M. Garza, G. V. Sanchez, S. Lau, S. DeLeon,
J. Org. Chem. 2000, 65, 8997–9000.
[8] a) D. A. Klumpp, A. Jones, S. Lau, S. DeLeon, M. Garza,
Synthesis 2000, 8, 1117–1120; b) D. A. Klumpp, S. L. Lau, J.
Org. Chem. 1999, 64, 7309–7311.
[9] D. A. Klumpp, S. Fredrick, S. Lau, K. K. Jin, R. Bau, G. K. S.
Prakash, G. A. Olah, J. Org. Chem. 1999, 64, 5152–5155.
[10] T. Yamazaki, S. Saito, T. Ohwada, K. Shudo, Tetrahedron Lett.
1995, 36, 5749–5752.
[11] a) G. A. Olah, Angew. Chem. Int. Ed. Engl. 1993, 32, 767–788;
b) V. G. Nenajdenko, N. E. Shevchenko, E. S. Balenkova, I. V.
Alabugin, Chem. Rev. 2003, 103, 229–282; c) G. A. Olah, D. A. [30] Y. Watanabe, Y. Tsuji, T. Kondo, R. Takeuchi, J. Org. Chem.
Klumpp, Acc. Chem. Res. 2004, 37, 211–220.
[12] G. A. Olah, R. H. Schlosberg, J. Am. Chem. Soc. 1968, 90,
6464–6467.
[13] R. Rendy, Y. Zhang, A. McElrea, A. Gomez, D. A. Klumpp,
J. Org. Chem. 2004, 69, 2340–2347.
[14] K. Yu. Koltunov, I. B. Repinskaya, Russ. J. Org. Chem. 1994,
30, 97–100.
[15] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria,
M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Mont-
gomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Mil-
1984, 49, 4451–4455.
[31] K. M. Broadus, S. R. Kass, J. Org. Chem. 2000, 65, 6566–6571.
[32] a) S. N. Salazkin, N. M. Fedoseenko, V. V. Korshak, S. V. Vino-
gradova, Izv. Akad. Nauk SSSR, Ser. Khim. 1978, 1, 137–142;
b) V. B. Milevskaya, G. I. Matushecheva, V. P. Kukhar, L. M.
Yagupolskii, Zh. Org. Khim. 1975, 11, 2449–2450; c) D. M.
Collington, D. H. Hey, C. W. Rees, E. L. Bradley, J. Chem. Soc.
C 1968, 8, 1021–1025.
Received: June 6, 2006
Published Online: September 4, 2006
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