G. K. Surya Prakash et al. / Tetrahedron Letters 52 (2011) 1217–1221
1221
Synthesis 1982, 1018–1020; (s) Nath, J.; Chaudhuri, M. K. Green Chem. Lett. Rev.
2008, 223–230.
5. Price, C. C.; Sears, C. A. J. Am. Chem. Soc. 1953, 75, 3276–3277.
6. Mueller, E.; Padeken, H. G. Chem. Ber. 1966, 99, 2971–2975.
7. Olah, G. A.; Ohannesian, L.; Arvanaghi, M.; Prakash, G. K. S. J. Org. Chem. 1984,
49, 2032–2034.
8. Schlubach, H. H.; Braun, A. Justus Liebigs Ann. Chem. 1959, 627, 28–34.
9. (a) Ranu, B. C.; Adak, L.; Banerjee, S. Aust. J. Chem. 2007, 60, 358–362; (b)
Podgorsek, A.; Stavber, S.; Zupan, M.; Iskra, J. Green Chem. 2007, 9, 1212–1218.
10. Olah, G. A.; Ramaiah, P.; Sandford, G.; Orlinkov, A.; Prakash, G. K. S. Synthesis
1994, 468–469.
17. General experimental procedure for the halogenation reaction: In a NalgeneÒ
bottle, to acetophenone (2 mmol) in dichloromethane (10 mL), potassium
nitrate (4 mmol) and chloro/bromotrimethylsilane (8 mmol) were added. The
heterogeneous mixture was stirred vigorously at 60 °C (for chlorination) or
room temperature (for bromination) until the reaction went to completion
(monitored by 1H NMR spectroscopy). The reaction mixture was then filtered
and solvent removed under reduced pressure. The chlorinated/brominated
acetophenone derivatives were obtained upon purification by flash
chromatography (silica gel) with hexane as eluent. The products were
characterized by comparing their spectroscopic data with those of the
authentic samples.
11. Prakash, G. K. S.; Panja, C.; Mathew, T.; Surampudi, V.; Olah, G. A. Org. Lett.
2004, 6, 2205–2207.
12. Vankar, P. S.; Reddy, M. V. R.; Vankar, Y. D. Org. Prep. Proced. Int. 1998, 30, 373–
400. and references therein.
13. Prakash, G. K. S.; Mathew, T.; Panja, C.; Olah, G. A. J. Org. Chem. 2007, 72, 5847–
5850.
14. (a) Lee, J. G.; Kwak, K. H.; Hwang, J. P. Tetrahedron Lett. 1990, 31, 6677–6680;;
(b) Lee, J. G.; Cha, H. T. Tetrahedron Lett. 1992, 33, 3167–3168.
15. (a) Goddard, D. R. J. Chem. Soc. 1958, 1955–1957; (b) Müller, E.; Padeken, H. G.
Chem. Ber. 1966, 99, 2971–2975; (c) Kaplan, R. B.; Schechter, H. Inorganic
Syntheses; McGraw-Hill Book Co.: New York, 1953. p 53; (d) Goddard, D. R.;
Hughes, E. D.; Ingold, C. K. J. Chem. Soc. 1950, 2559–2575.
16. (a) Batey, H. H.; Sisler, H. H. J. Am. Chem. Soc. 1952, 74, 3410; (b) Collis, M. J.;
Goddard, D. R. J. Chem. Soc. 1958, 1952–1955; (c) Gintz, F. P.; Goddard, D. R.;
Collis, M. J. J. Chem. Soc. 1958, 445–451;; (d) Collis, M. J.; Gintz, F. P.; Goddard,
D. R.; Hebdon, E. A.; Minkoff, G. J. J. Chem. Soc 1958, 438–445;; (e) Collis, M. J.;
Gintz, F. P.; Goddard, D. R.; Hebdon, E. A. Chem. Ind. 1955, 1742–1743.
18. Schmidt, M.; Schmidbaur, H. Angew. Chem. 1959, 71, 220.
19. (a) Boughriet, A.; Coumare, A.; Fischer, J. C.; Wartel, M. Int. J. Chem. Kinet. 1988,
20, 775–786; (b) Ray, J. D.; Ogg, R. A. J. Chem. Phys. 1959, 31, 168–171.
20. GAUSSIAN 09, Revision A.02, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria,
G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.;
Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A.
F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.;
Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai,
H.; Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.;
Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand,
J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.;
Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.;
Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.;
Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.;
Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas,
Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc.,
Wallingford CT, 2009.