m-Chloroperbenzoic Acid
A. Somasekar Rao
Indian Institute of Chemical Technology, Hyderabad, India
Search for more papers by this authorH. Rama Mohan
Indian Institute of Chemical Technology, Hyderabad, India
Search for more papers by this authorA. Somasekar Rao
Indian Institute of Chemical Technology, Hyderabad, India
Search for more papers by this authorH. Rama Mohan
Indian Institute of Chemical Technology, Hyderabad, India
Search for more papers by this authorAbstract
[937-14-4] C7H5ClO3 (MW 172.57)
InChI = 1S/C7H5ClO3/c8-6-3-1-2-5(4-6)7(9)11-10/h1-4,10H
InChIKey = NHQDETIJWKXCTC-UHFFFAOYSA-N
(electrophilic reagent capable of reacting with many functional groups; delivers oxygen to alkenes, sulfides, selenides, and amines)
Alternate Name: m-CPBA; MCPBA.
Physical Data: mp 92–94 °C.
Solubility: soluble in CH2Cl2, CHCl3, 1,2-dichloroethane, ethyl acetate, benzene, and ether; slightly soluble in hexane; insoluble in H2O.
Form Supplied in: white powder, available with purity of 50%, 85%, and 98% (the rest is 3-chlorobenzoic acid and water).
Analysis of Reagent Purity: iodometry.2
Purification commercial material (purity 85%) is washed with a phosphate buffer of pH 7.5 and dried under reduced pressure to furnish reagent with purity >99%.3
Handling, Storage, and Precautions: pure m-CPBA is shock sensitive and can deflagrate;4 potentially explosive, and care is required while carrying out the reactions and during workup.5 Store in polyethylene containers under refrigeration.
References
- 1 (a) Swern, D., Organic Peroxides; Wiley: New York, 1971; Vol 2, pp 355–533. (b) Plesnicar, B. Organic Chemistry; Academic: New York, 1978; Vol. 5 C, pp 211–294. (c) Rao, A. S., Comprehensive Organic Synthesis 1991, 7, Chapter 3.1.
- 2 McDonald, R. N.; Steppel, R. N.; Dorsey, J. E., Org. Synth. 1970, 50, 15.
- 3 (a) Schwartz, N. N.; Blumbergs, J. H., J. Org. Chem. 1964, 29, 1976. (b) Nakayama, J.; Kamiyama, H., Tetrahedron Lett. 1992, 33, 7539.
- 4 Brougham, P.; Cooper, M. S.; Cummerson, D. A.; Heany, H.; Thompson, N., Synthesis 1987, 1015.
- 5 Hazards in the Chemical Laboratory; S. G. Luxon, Ed.; Royal Society of Chemistry: Cambridge, 1992.
- 6 (a) Ishikawa, K.; Charles, H. C.; Griffin, G. W., Tetrahedron Lett. 1977, 427. (b) Srebnik, M.; Mechoulam, R., Synthesis 1983, 1046.
- 7 Berti, G., Top. Stereochem. 1973, 7, 93.
- 8 (a) Woods, K. W.; Beak, P., J. Am. Chem. Soc. 1991, 113, 6281. (b) Bartlett, P. D., Rec. Chem. Prog. 1950, 11, 47 (cited in Ref. 1a).
- 9 (a) Camps, F.; Coll, J.; Messeguer, A.; Pujol, F., J. Org. Chem. 1982, 47, 5402. (b) Chai, K.-B.; Sampson, P., Tetrahedron Lett. 1992, 33, 585.
- 10 Paquette, L. A.; Barrett, J. H., Org. Synth. 1969, 49, 62.
- 11 (a) Wender, P. A.; Zercher, C. K., J. Am. Chem. Soc. 1991, 113, 2311. (b) Philippo, C. M. G.; Vo, N. H.; Paquette, L. A., J. Am. Chem. Soc. 1991, 113, 2762.
- 12 Bach, R. D.; Knight, J. W., Org. Synth. 1981, 60, 63.
- 13 (a) Kishi, Y.; Aratani, M.; Tanino, H.; Fukuyama, T.; Goto, T., Chem. Commun./J. Chem. Soc., Chem. Commun. 1972, 64. (b) Valente, V. R.; Wolfhagen, J. L., J. Org. Chem. 1966, 31, 2509.
- 14 Anderson, W. K.; Veysoglu, T., J. Org. Chem. 1973, 38, 2267. (b) Imuta, M.; Ziffer, H., J. Org. Chem. 1979, 44, 1351.
- 15 Urones, J. G.; Marcos, I. S.; Basabe, P.; Alonso, C.; Oliva, I. M.; Garrido, N. M.; Martin, D. D.; Lithgow, A. M., Tetrahedron 1993, 49, 4051.
- 16 Bäckvall, J.-E.; Juntunen, S. K., J. Org. Chem. 1988, 53, 2398.
- 17 Hudlicky, T.; Price, J. D.; Rulin, F.; Tsunoda, T., J. Am. Chem. Soc. 1990, 112, 9439.
- 18 Marsh, E. A., Synlett 1991, 529.
- 19 Brown, H. C.; Kawakami, J. H.; Ikegami, S., J. Am. Chem. Soc. 1970, 92, 6914.
- 20 Devreese, A. A.; Demuynck, M.; De Clercq, P. J.; Vandewalle, M., Tetrahedron 1983, 39, 3049.
- 21 Still, W. C.; Romero, A. G., J. Am. Chem. Soc. 1986, 108, 2105.
- 22 Schneider, A.; Séquin, U., Tetrahedron 1985, 41, 949.
- 23 Johnson, C. R.; Tait, B. D.; Cieplak, A. S., J. Am. Chem. Soc. 1987, 109, 5875.
- 24 (a) Henbest, H. B.; Wilson, R. A. L., J. Chem. Soc. 1957, 1958. (b) Itoh, T.; Jitsukawa, K.; Kaneda, K.; Teranishi, S., J. Am. Chem. Soc. 1979, 101, 159.
- 25 Wipf, P.; Kim, Y., J. Org. Chem. 1993, 58, 1649.
- 26 (a) Kim, G.; Chu-Moyer, M. Y.; Danishefsky, S. J.; Schulte, G. K., J. Am. Chem. Soc. 1993, 115, 30. (b) Fukuyama, T.; Xu, L.; Goto, S., J. Am. Chem. Soc. 1992, 114, 383.
- 27 (a) Sharpless, K. B.; Verhoeven, T. R., Aldrichim. Acta 1979, 12, 63. (b) Rossiter, B. E.; Verhoeven, T. R.; Sharpless, K. B., Tetrahedron Lett. 1979, 4733. (c) Adam, W.; Nestler, B., J. Am. Chem. Soc. 1993, 115, 5041.
- 28 Kočovský, P.; Starý, I., J. Org. Chem. 1990, 55, 3236.
- 29 Murphy, P. J.; Russel, A. T.; Procter, G., Tetrahedron Lett. 1990, 31, 1055.
- 30 Fleming, I.; Sarkar, A. K.; Thomas, A. P., Chem. Commun./J. Chem. Soc., Chem. Commun. 1987, 157.
- 31 Johnson, M. R.; Kishi, Y., Tetrahedron Lett. 1979, 4347.
- 32 Roush, W. R.; Straub, J. A.; Brown, R. J., J. Org. Chem. 1987, 52, 5127.
- 33 Sakai, N.; Ohfune, Y., J. Am. Chem. Soc. 1992, 114, 998.
- 34 Lewis, M. D.; Menes, R., Tetrahedron Lett. 1987, 28, 5129.
- 35 Fukuyama, T.; Wang, C.-L. J.; Kishi, Y., J. Am. Chem. Soc. 1979, 101, 260.
- 36 Paquette, L. A.; Lin, H.-S.; Gallucci, J. C., Tetrahedron Lett. 1987, 28, 1363.
- 37 (a) Rubottom, G. M.; Gruber, J. M., J. Org. Chem. 1978, 43, 1599. (b) Rubottom, G. M.; Gruber, J. M.; Juve, H. D.; Charleson, D. A., Org. Synth. 1986, 64, 118.
- 38 (a) Herlem, D.; Kervagoret, J.; Yu, D.; Khuong-Huu, F.; Kende, A. S., Tetrahedron 1993, 49, 607. (b) Crimmins, M. T.; Jung, D. K.; Gray, J. L., J. Am. Chem. Soc. 1993, 115, 3146.
- 39 Rubottom, G. M.; Marrero, R., J. Org. Chem. 1975, 40, 3783.
- 40 Hassner, A.; Reuss, R. H.; Pinnick, H. W., J. Org. Chem. 1975, 40, 3427.
- 41 Horiguchi, Y.; Nakamura, E.; Kuwajima, I., Tetrahedron Lett. 1989, 30, 3323.
- 42 Shimshock, S. J.; Waltermire, R. E.; DeShong, P., J. Am. Chem. Soc. 1991, 113, 8791.
- 43 Honda, T.; Kobayashi, Y.; Tsubuki, M., Tetrahedron 1993, 49, 1211.
- 44 Zhou, W.-S.; Lu, Z.-H.; Wang, Z.-M., Tetrahedron 1993, 49, 2641.
- 45 Krow, G. R., Comprehensive Organic Synthesis 1991, 7, Chapter 5, 1.
- 46 Feldman, K. S.; Wu, M.-J.; Rotella, D. P., J. Am. Chem. Soc. 1990, 112, 8490.
- 47 Bakale, R. P.; Scialdone, M. A.; Johnson, C. R., J. Am. Chem. Soc. 1990, 112, 6729.
- 48 Gilbert, K. E.; Borden, W. T., J. Org. Chem. 1979, 44, 659.
- 49 Robinson, C. H.; Milewich, L.; Hofer, P., J. Org. Chem. 1966, 31, 524.
- 50 Taylor, E. C.; Tseng, C.-P.; Rampal, J. B., J. Org. Chem. 1982, 47, 552.
- 51 Jasys, V. J.; Kelbaugh, P. R.; Nason, D. M.; Phillips, D.; Rosnack, K. J.; Saccomano, N. A.; Stroh, J. G.; Volkmann, R. A., J. Am. Chem. Soc. 1990, 112, 6696.
- 52 Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, S. V.; Dai, W.-M.; Chadha, R. K., J. Am. Chem. Soc. 1992, 114, 8890.
- 53 Craig, J. C.; Purushothaman, K. K., J. Org. Chem. 1970, 35, 1721.
- 54 Reetz, M. T.; Lauterbach, E. H., Tetrahedron Lett. 1991, 32, 4481.
- 55 Ali, Sk. A.; Wazeer, M. I. M., Tetrahedron 1993, 49, 4339.
- 56 Hwu, J. R.; Robl, J. A.; Gilbert, B. A., J. Am. Chem. Soc. 1992, 114, 3125.
- 57 Vishwakarma, L. C.; Stringer, O. D.; Davis, F. A., Org. Synth. 1988, 66, 203.
- 58 Duraisamy, M.; Walborsky, H. M., J. Org. Chem. 1984, 49, 3410.
- 59 (a) Sekine, M.; Iimura, S.; Nakanishi, T., Tetrahedron Lett. 1991, 32, 395. (b) Beaucage, S. L.; Iyer, R. P., Tetrahedron 1992, 48, 2223.
- 60 Cullis, P. M., Chem. Commun./J. Chem. Soc., Chem. Commun. 1984, 1510.
- 61 Filby, W. G.; Günther, K.; Penzhorn, R. D., J. Org. Chem. 1973, 38, 4070.
- 62 Trost, B. M.; Salzmann, T. N.; Hiroi, K., J. Am. Chem. Soc. 1976, 98, 4887.
- 63 Madesclaire, M., Tetrahedron 1986, 42, 5459.
- 64 Evans, D. A.; Faul, M. M.; Colombo, L.; Bisaha, J. J.; Clardy, J.; Cherry, D., J. Am. Chem. Soc. 1992, 114, 5977.
- 65 (a) Wang, X.; Ni, Z.; Lu, X.; Smith, T. Y.; Rodriguez, A.; Padwa, A., Tetrahedron Lett. 1992, 33, 5917. (b) DeLucchi, O.; Fabri, D., Synlett 1990, 287.
- 66 Block, E.; Putman, D., J. Am. Chem. Soc. 1990, 112, 4072.
- 67 Le Nocher, A. M.; Metzner, P., Tetrahedron Lett. 1991, 32, 747.
- 68 Kuimelis, R. G.; Nambiar, K. P., Tetrahedron Lett. 1993, 34, 3813.
- 69 Kochhar, K. S.; Cottrell, D. A.; Pinnick, H. W., Tetrahedron Lett. 1983, 24, 1323.
- 70 (a) Reich, H. J.; Shah, S. K., J. Am. Chem. Soc. 1975, 97, 3250. (b) Danheiser, R. L.; Choi, Y. M.; Menichincheri, M.; Stoner, E. J., J. Org. Chem. 1993, 58, 322.
- 71 Toshimitsu, A.; Hirosawa, C.; Tanimoto, S.; Uemura, S., Tetrahedron Lett. 1992, 33, 4017.
- 72 Yamamoto, S.; Itani, H.; Tsuji, T.; Nagata, W., J. Am. Chem. Soc. 1983, 105, 2908.
- 73 Boeckman, Jr., R. K.; Thomas, E. W., J. Am. Chem. Soc. 1979, 101, 987.
- 74 Sanghvi, Y. S.; Rao, A. S., J. Heterocycl. Chem. 1984, 21, 317.
- 75 (a) Murray, R. W., C. R. Hebd. Seances Acad. Sci. 1989, 89, 1187. (b) Halcomb, R. L.; Danishefsky, S. J., J. Am. Chem. Soc. 1989, 111, 6661. (c) Adam, W.; Hadjiarapoglou, L.; Wang, X., Tetrahedron Lett. 1989, 30, 6497. (d) Adam, W.; Curci, R.; Edwards, J. O., Ann. Chim. (Rome) 1989, 22, 205.
- 76
Hachtel, J.;
Gais, H. J.,
Eur. J. Org. Chem.
2000,
1457–1465.
10.1002/(SICI)1099-0690(200004)2000:8<1457::AID-EJOC1457>3.0.CO;2-G CAS Web of Science® Google Scholar
- 77 Takeda, K.; Nakajima, A.; Takeda, M.; Okamoto, Y.; Sato, T.; Yoshii, E.; Koizumi, T.; Shiro, M., J. Am. Chem. Soc. 1998, 120, 4947–4959.
- 78 (a) Adam, W.; Peters, K.; Peters, E. M.; Schambony, S. B., J. Am. Chem. Soc. 2001, 123, 7228–7232. (b) Adam, W.; Schambony, S. B., Org. Lett. 2001, 3, 79–82. (c) Adam, W.; Bosio, S. G.; Wolff, B. T., Org. Lett. 2003, 5, 819–822.
- 79 Davies, S. G.; Key, M. S.; Rodriguez-Solla, H.; Sanganee, H. J.; Savory, E. D.; Smith, A. D., Synlett 2003, 1659–1662.
- 80 Kato, K.; Suemune, H.; Sakai, K., Tetrahedron Lett. 1994, 35, 3103–3104.
- 81 (a) Crich, D.; Mataka, J.; Zakharov, L. N.; Rheingold, A. L.; Wink, D. J., J. Am. Chem. Soc. 2002, 124, 6028–6036.
- 82 (a) Jenmalm, A.; Berts, W.; Li, Y. L.; Luthman, K.; Csoregh, I.; Hacksell, U., J. Org. Chem. 1994, 59, 1139–1148. (b) Jenmalm, A.; Berts, W.; Luthman, K.; Csoregh, I.; Hacksell, U., J. Org. Chem. 1995, 60, 1026–1032.
- 83 Maruyama, K.; Ueda, M.; Sasaki, S.; Iwata, Y.; Miyazawa, M.; Miyashita, M., Tetrahedron Lett. 1998, 39, 4517–4520.
- 84 Bellucci, G.; Catelani, G.; Chiappe, C.; Dandrea, F., Tetrahedron Lett. 1994, 35, 8433–8436.
- 85 Li, Y. Q.; Thiemann, T.; Sawada, T.; Mataka, S.; Tashiro, M., J. Org. Chem. 1997, 62, 7926–7936.
- 86 Furukawa, N.; Zhang, S. Z.; Sato, S.; Higaki, M., Heterocycles 1997, 44, 61–66.
- 87 Hanna, I.; Michaut, V., Org. Lett. 2000, 2, 1141–1143.
- 88 Crudden, C. M.; Chen, A. C.; Calhoun, L. A., Angew. Chem. Int. Ed. 2000, 39, 2852–2855.
- 89 Itoh, Y.; Yamanaka, M.; Mikami, K., Org. Lett. 2003, 5, 4803–4806.
- 90 Kobayashi, S.; Tanaka, H.; Amii, H.; Uneyama, K., Tetrahedron 2003, 59, 1547–1552.
- 91 Hunt, K. W.; Grieco, P. A., Org. Lett. 2000, 2, 1717–1719.
- 92 Kotsuki, H.; Arimura, K.; Araki, T.; Shinohara, T., Synlett 1999, 462–464.
- 93 Alam, M. M.; Varala, R.; Adapa, S. R., Syn. Comm. 2003, 33, 3035–3040.
- 94 Luzzio, F. A.; Bobb, R. A., Tetrahedron Lett. 1997, 38, 1733–1736.
- 95 Lakhrissi, M.; Carchon, G.; Schlama, T.; Mioskowski, C.; Chapleur, Y., Tetrahedron Lett. 1998, 39, 6453–6456.
- 96 Lakhrissi, M.; Chapleur, Y., Tetrahedron Lett. 1998, 39, 4659–4662.
- 97 An, G. I.; Rhee, H., Synlett 2003, 876–878.
- 98 Kim, S. Y.; An, G. I.; Rhee, H., Synlett 2003, 112–114.
- 99 Palucki, M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N., J. Am. Chem. Soc. 1994, 116, 9333–9334.
- 100 Palucki, M.; McCormick, G. J.; Jacobsen, E. N., Tetrahedron Lett. 1995, 36, 5457–5460.
- 101 Prasad, J. S.; Vu, T.; Totleben, M. J.; Crispino, G. A.; Kacsur, D. J.; Swaminathan, S.; Thornton, J. E.; Fritz, A.; Singh, A. K., Org. Process. Res. Dev. 2003, 7, 821–827.
- 102 Andrus, M. B.; Poehlein, B. W., Tetrahedron Lett. 2000, 41, 1013–1014.
- 103 O'Neil, I. A.; Cleator, E.; Tapolczay, D. J., Tetrahedron Lett. 2001, 42, 8247–8249.
- 104 Sammelson, R. E.; Kurth, M. J., Tetrahedron Lett. 2001, 42, 3419–3422.
- 105 Ma, D. W.; Xia, C. F.; Tian, H. Q., Tetrahedron Lett. 1999, 40, 8915–8917.
- 106 Luzzio, F. A.; Zacherl, D. P.; Figg, W. D., Tetrahedron Lett. 1999, 40, 2087–2090.