Gas-phase Polar Cycloadditions

The dilute gas-phase environment of mass spectrometers provides versatile and convenient medium in which chemists can form a great variety of ionic species and study their intrinsic reactivity exploring reaction mechanisms and screening for new reactions and their applications. Recent and illustrative examples of gas-phase polar cycloadditions of even and odd-electrons ions, which have been observed (some for the first time) in the solvent- and counter ion-free environment of mass spectrometers, are presented. Synthetic and analytical applications of such reactions and correlations with analogous reactions observed in solution are also discussed. © 2004 Elsevier B.V. All rights reserved.2353263278Carruthers, W., Cycloadditon Reactions in Organic Synthesis, p. 1990. , PergamonDiels, O., Alder, K., (1928) Justus Liebigs Ann. Chem., 460, p. 98(1997) IUPAC Compendium of Chemical Terminology, Second Ed.Schmidt, R.R., (1973) Angew. Chem. Int. Edit., 12, p. 212Bauld, N.L., Bellville, D.J., Harirchian, B., Lorenz, K.T., Pabon Jr., R.A., Reynolds, D.W., Wirth, D.D., Marsh, B.K., (1987) Acc. Chem. Res., 20, p. 371Dass, C., (1990) Mass Spectrom. Rev., 9, p. 1Gronert, S., (2001) Chem. Rev., 101, p. 329Kuck, D., Mormann, M., (2002) The Chemistry of Dienes and Polyenes, 2. , Rappoport, Z.WileyHeinrich, N., Koch, W., Morrow, J.C., Schwarz, H., (1988) J. Am. Chem. Soc., 110, p. 6332Wilkins, C.L., Gross, M.L., (1971) J. Am. Chem. Soc., 93, p. 895Van Doorn, R., Nibbering, N.M.M., Ferrer-Correia, A.J.V., Jennings, K.R., (1978) Org. Mass Spectrom., 13, p. 729Vairamani, M., Mirza, U., Srinivas, R., (1990) Mass Spectrom. Rev., 9, p. 253Einhorn, J., Duffault, J.M., Virelizier, H., Tabet, J.C., (1988) Rapid Commun. Mass Spectrom., 2, p. 112Colorado, A., Barket, D.J., Hurst, J.M., Shepson, P.B., (1998) Anal. Chem., 70, p. 5129Bouchoux, G., Salpin, J.-Y., (1994) Rapid Commun. Mass Spectrom., 8, p. 325Bouchoux, G., Nguyen, M.T., Salpin, J.-Y., (2000) J. Phys. Chem., 104, p. 5778Grützmacher, H.-F., Barkow, A., (1997) Acta Chem. Scand., 51, p. 619Becker, H., Javahery, G., Petrie, S., Bohme, D.K., (1994) J. Phys. Chem., 98, p. 5591Shay, B.J., Eberlin, M.N., Cooks, R.G., Wesdemiotis, C., (1992) J. Am. Soc. Mass Spectrom., 3, p. 518Goerbbert, D.J., Liu, X., Wenthold, P.G., (2004) J. Am Soc. Mass Spectrom., 15, p. 114Hammerum, S., (1988) Mass Spectrom. Rev., 7, p. 123Stirk, K.M., Kiminkinen, M.L.K., Kenttämaa, H.I., (1992) Chem. Rev., 92, p. 1649Yates, B.F., Bouma, W.J., Radom, L., (1986) Tetrahedron, 42, p. 6225Moraes, L.A.B., Eberlin, M.N., (1998) J. Am. Chem. Soc., 120, p. 11136Eberlin, M.N., Sorrilha, A.E.P.M., Gozzo, F.C., Pimpim, R., (1997) J. Am. Chem. Soc., 119, p. 3550Lange, C., (1993) Org. Mass Spectrom., 28, p. 1285Mourgues, P., Audier, H.E., Hammerum, S., (1994) Rapid Commun. Mass Spectrom., 8, p. 53Gerbaux, P., Haverbeke, Y.V., Flammang, R., (2003) J. Am. Soc. Mass Spectrom., 14, p. 241Olah, G.A., Reddy, V.P., Prakash, G.K.S., (1992) Chem. Rev., 92, p. 69Holman, R.W., Plocica, J., Blair, L., Giblin, D., Gross, M.L., (2001) J. Phys. Org. Chem., 14, p. 17Eberlin, M.N., (1997) Mass Spectrom. Rev., 16, p. 113Eberlin, M.N., Mass Spectrom. Rev., , submitted for publicationEberlin, M.N., Cooks, R.G., (1993) J. Am. Chem. Soc., 115, p. 9226Meurer, E.C., Eberlin, M.N., (2002) J. Mass Spectrom., 37, p. 146Meurer, E.C., Moraes, L.A.B., Eberlin, M.N., (2001) Int. J. Mass Spectrom., 212, p. 445Eberlin, M.N., Majumdar, T.K., Cooks, R.G., (1992) J. Am. Chem. Soc., 114, p. 2884Juliano, V.J., Gozzo, F.C., Eberlin, M.N., Kascheres, C., (1996) Anal. Chem., 68, p. 1328Sharifi, M., Einhorn, J., (1999) Int. J. Mass Spectrom., 190-191, p. 253Eberlin, M.N., Morgon, N.H., Yang, S.S., Shay, B.J., Cooks, R.G., (1995) J. Am. Soc. Mass Spectrom., 6, p. 1Eberlin, M.N., Basher, M., Riveros, J.M., J. Mass Spectrom, , submitted for publicationGozzo, F.C., Sorrilha, A.E.P.M., Eberlin, M.N., (1996) J. Chem. Soc. Perkin Trans., p. 587Lu, L., Yang, S.S., Wang, Z., Cooks, R.G., Eberlin, M.N., (1995) J. Mass Spectrom., 30, p. 581Lemos, A.D., Sparrapan, R., Eberlin, M.N., (2003) J. Mass Spectrom., 38, p. 305Brodbelt, J.S., (1997) Mass Spectrom. Rev., 16, p. 91Keough, T., (1982) Anal. Chem., 54, p. 2540Ma, L., Liu, Z., Wang, W., Guo, X., Liu, S., (1999) J. Phys. Chem. a, 103, p. 8634Van Tilborg, M.W.E.M., Van Doorn, R., Nibbering, N.M.M., (1980) Org. Mass Spectrom., 15, p. 152Gozzo, F.C., Eberlin, M.N., (1999) J. Org. Chem., 64, p. 2188Kauffmann, T., (1965) Angew. Chem., 77, p. 557Sparrapan, R., Mendes, M.A., Carvalho, M., Eberlin, M.N., (2000) Chem. Eur. J., 6, p. 321Eberlin, M.N., Augusti, R., J. Mass Spectrom., , submitted for publicationD'Oca, M.G.M., Moraes, L.A.B., Pilli, R.A., Eberlin, M.N., (2001) J. Org. Chem., 66, p. 3854Needleman, S.B., Chang-Kuo, M.C., (1962) Chem. Rev., 62, p. 45Tomazela, D.M., Moraes, L.A.B., D'Oca, M.G.M., Pilli, R.A., Eberlin, M.N., (2002) J. Org. Chem., 67, p. 4652Van Pelt, C.K., Brenna, J.T., (1999) Anal. Chem., 71, p. 1981Pelt, C.K., Carpenter, B.K., Brenna, J.T., (1999) J. Am. Soc. Mass. Spectrom., 10, p. 1253Bernardi, F., Cacace, F., Petris, G., Pepi, F., Rossi, I., Troiani, A., (2000) Chem. Eur. J., 6, p. 537Boger, D.L., Weinreb, S.N., (1987) Hetero Diels-Alder Methodology in Organic Synthesis, , H.H. Wasserman (Ed.), New York, Academic PressAugusti, R., Gozzo, F.C., Moraes, L.A.B., Sparrapan, R., Eberlin, M.N., (1998) J. Org. Chem., 63, p. 4889Meurer, E.C., Moraes, L.A.B., Eberlin, M.N., (2001) Int. J. Mass Spectrom., 212, p. 445Meurer, E.C., Sparrapan, R., Eberlin, M.N., (2003) J. Mass Spectrom., 38, p. 1075Meurer, E.C., Chen, H., Riter, L., Cotte-Rodriguez, I., Eberlin, M.N., Cooks, R.G., (2004) Chem. Commun., p. 40Cowley, A.H., (1985) R.A. Kemp. Chem. Rev., 85, p. 367Solovieva, S.E., Gruner, M., Antipin, I.S., Habicher, W.D., Konovalov, A.I., (2001) Org. Lett., 3, p. 1299Gevrey, S., Taphanel, M.-H., Morizur, J.-P., (1998) J. Mass Spectrom., 33, p. 399Sabino, A.A., Eberlin, M.N., Moraes, L.A.B., Laali, K.K., (2003) Org. Biomol. Chem., 1, p. 395Moraes, L.A.B., Eberlin, M.N., Laali, K.K., (2001) Organometallics, 20, p. 4863Bakhtiar, R., Drader, J.D., Jacobson, D.B., (1992) J. Am. Chem. Soc., 114, p. 8304Schroeter, K., Schalley, C.A., Wesendrup, R., Schöder, D., Schwarz, H., (1997) Organometallics, 16, p. 986Chen, Q., Sioma, C., Kan, S.Z., Freiser, B.S., (1998) Int. J. Mass Spectrom., 180, p. 231Fenn, J.B., Mann, M., Meng, C.K., Wong, S.F., Whitehouse, C.M., (1989) Science, 246, p. 64Huang, E.C., Wachs, T., Conboy, J.J., Henion, J.D., (1990) Anal. Chem., 62, p. 713Hilderling, C., Adlhart, C., Chen, P., (1998) Angew. Chem. Int. Ed., 37, p. 2685Chen, P., (2003) Angew. Chem. Int. Ed., 42, p. 2832Sabino, A.A., MacHado, A.H.L., Correia, C.R.D., Eberlin, M.N., (2004) Angew. Chem. Int. Ed., 43, p. 2514Meurer, E.C., Santos, L.S., Pilli, R.A., Eberlin, M.N., (2003) Org. Lett., 5, p. 1391Choi, S.H., Cooley, R.B., Hakemian, A.S., Larrabee, Y.C., Bunt, R.C., Maupas, S.D., Muller, J.G., Burrows, C.J., (2004) J. Am. Chem. Soc., 126, p. 591Schuster, D.I., Cao, J.R., Kaprinidis, N., Wu, Y.H., Jensen, A.W., Lu, Q.Y., Wang, H., Wilson, S.R., (1996) J. Am. Chem. Soc., 118, p. 5639Meyer, S., Metzger, J.O., (2003) Anal. Bioanal. Chem., 377, p. 1108Meyer, S., Koch, R., Metzger, J.O., (2003) Angew. Chem. Int. Ed., 42, p. 4700Meurer, E.C., Sabino, A.A., Eberlin, M.N., (2003) Anal. Chem., 75, p. 4701Wentrup, C., Heilmayer, W., Kollenz, G., (1994) Synthesis, 343, p. 1219Eberlin, M.N., Moraes, L.A.B., J. Mass Spectrom., , submitted for publicatio