dc.creatorAbella C.A.M.
dc.creatorBenassi M.
dc.creatorSantos L.S.
dc.creatorEberlin M.N.
dc.creatorCoelho F.
dc.date2007
dc.date2015-06-30T18:37:23Z
dc.date2015-11-26T15:01:26Z
dc.date2015-06-30T18:37:23Z
dc.date2015-11-26T15:01:26Z
dc.date.accessioned2018-03-28T22:12:28Z
dc.date.available2018-03-28T22:12:28Z
dc.identifier
dc.identifierJournal Of Organic Chemistry. , v. 72, n. 11, p. 4048 - 4054, 2007.
dc.identifier223263
dc.identifier10.1021/jo062556w
dc.identifierhttp://www.scopus.com/inward/record.url?eid=2-s2.0-34249796694&partnerID=40&md5=93344b4d2b4fa435cc4bfca7f17cdb66
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/104034
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/104034
dc.identifier2-s2.0-34249796694
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1256280
dc.description(Chemical Equation Presented) Using direct infusion electrospray ionization mass and tandem mass spectrometric experiments [ESI-MS(/MS)], we have performed on-line monitoring of some reactions used to form Tröger's bases. Key intermediates, either as cationic species or as protonated forms of neutral species, have been intercepted and characterized. The role of urotropine as the methylene source in these reactions has also been accessed. Reaction pathways shown by ESI-MS(/MS) have been probed by gas-phase ion/molecule reactions, and an expanded mechanism for Tröger's base formation based on the mass spectrometric data has been elaborated. © 2007 American Chemical Society.
dc.description72
dc.description11
dc.description4048
dc.description4054
dc.descriptionTröger, J., (1887) J. Prakt. Chem, 36, p. 225
dc.descriptionValík, M., Strongin, R.M., Král, V., (2005) Supramol. Chem, 17, p. 347. , For a recent review, see
dc.description(1992) Fascinating Molecules in Organic Chemistry, pp. 237-249. , Vögtle, F, Ed, John Wiley: New York
dc.descriptionPrelog, V., Wieland, P., (1944) Helv. Chim. Acta, 27, p. 1127
dc.descriptionAdrian Jr., J.C., Wilcox, C.S., (1989) J. Am. Chem. Soc, 111, p. 8055
dc.descriptionCrossley, M.J., Hambley, T.W., Mackay, L.G., Try, A.C., Walton, R., (1995) J. Chem. Soc. Chem. Commun, 10, p. 1077
dc.descriptionCrossley, M.J., Mackay, L.G., Try, A.C., (1995) J. Chem. Soc. Chem. Commun, 18, p. 1925
dc.descriptionGoswami, S., Ghosh, K., (1997) Tetrahedron Lett, 38, p. 4503
dc.descriptionManjula, A., Nagarajan, M., (1997) Tetrahedron, 53, p. 11859
dc.descriptionHansson, A.P., Norrby, P., Wärnmark, K., (1998) Tetrahedron Lett, 39, p. 4565
dc.descriptionGoswami, S., Ghosh, K., Dasgupta, S., (2000) J. Org. Chem, 65, pp. 1907-1914
dc.descriptionWilcox, C.S., (1985) Tetrahedron Lett, 26, p. 5749
dc.descriptionWilcox, C.S., Cowart, M.D., (1986) Tetrahedron Lett, 27, p. 5563
dc.descriptionWilcox, C.S., Adrian Jr., J.C., Webb, T.H., Zawacki, F.J., (1992) J. Am. Chem. Soc, 114, p. 10189
dc.descriptionWebb, T.H., Wilcox, C.S., (1993) Chem. Soc. Rev, 383
dc.descriptionWilen, S.H., Qi, J.Z., Williard, P.G., (1991) J. Org. Chem, 56, p. 485
dc.descriptionZhao, L., Xu, J.J., Zhang, G., Bu, X., Shionoya, M., (1999) Opt. Lett, 24, p. 1793
dc.descriptionAbella, C.A.M., Rodembusch, F.S., Stefani, V., (2004) Tetrahedron Lett, 45, p. 5601
dc.descriptionDeprez, N.R., McNitt, K.A., Petersen, M.E., Brown, R.G., Lewis, D.E., (2005) Tetrahedron Lett, 46, p. 2149
dc.descriptionJohnson, R.A., Gorman, R.R., Wnuk, R.J., Crittenden, N.J., Aiken, J.W., (1993) J. Med. Chem, 36, p. 3202
dc.descriptionGoldberg, Y., Alper, H., (1995) Tetrahedron Lett, 36, p. 369
dc.descriptionYashima, E., Akashi, M., Miyauchi, N., (1991) Chem. Lett, 6, p. 1017
dc.descriptionTatibouët, A., Demeunynck, M., Andraud, C., Collet, A., Shomme, J., (1999) Chem. Commun, 2, p. 161
dc.descriptionLaine, W., Demeunynck, M., Lhome, J., (2000) Biochem. Biophys. Res. Commun, 273, p. 681
dc.descriptionBaldeyrou, B., Tardy, C., Bailly, C., Colson, P., Houssier, C., Charmantray, F., Demeunynck, M., (2002) Eur. J. Med. Chem, 37, p. 315
dc.descriptionPardo, C., Sesmilo, E., Gutiérrez-Puebla, E., Monge, A., Elguero, J., Fruchier, A., (2001) J. Org. Chem, 66, p. 1607
dc.descriptionMas, T., Pardo, C., Elguero, J., (2004) Mendeleev Commun, 6, p. 235
dc.descriptionDolenský, B., Valík, M., Sýkora, D., Král, V., (2005) Org. Lett, 7, p. 67
dc.descriptionHansson, A., Wixe, T., Bergquist, K.-E., Wärnmark, K., (2005) Org. Lett, 7, pp. 2019-2022
dc.descriptionLöb, W., (1898) Z. Elektrochem, 4, p. 428
dc.descriptionGoecke, E., (1903) Z. Elektrochem, 9, p. 470
dc.descriptionLepetit, R., Maimeri, C., (1917) Atti. Accad. Naz. Lincei, 26, p. 558
dc.descriptionLepetit, R., Maffei, G., Maimeri, C., (1927) Gazz. Chim. Ital, 57, p. 862
dc.descriptionEisner, A., Wagner, E.C., (1934) J. Am. Chem. Soc, 56, p. 1938
dc.descriptionSpielman, M.A., (1935) J. Am. Chem. Soc, 57, p. 583
dc.descriptionLarson, S.B., Wilcox, C.S., (1986) Acta Crystallogr., Sect. C, 42, p. 224
dc.descriptionPardo, C., Alkorta, I., Elguero, J., (2006) Tetrahedron: Asymmetry, 17, pp. 191-198
dc.descriptionWagner, E.C., (1935) J. Am. Chem. Soc, 57, p. 1296
dc.descriptionMiller, T.R., Wagner, E.C., (1941) J. Am. Chem. Soc, 63, p. 832
dc.descriptionFarrar, W.V., (1964) J. Appl. Chem, 14, p. 389
dc.descriptionCooper, F.C., Partridge, M.W., (1955) J. Chem. Soc, (PART 3), p. 991
dc.descriptionThe data acquired with veratrol are similar to those obtained with formaldehyde, hence such results are not discussedGriep-Raming, J., Meyer, S., Bruhn, T., Metzger, J.O., (2002) Angew. Chem., Int. Ed, 41, p. 2738
dc.descriptionMeyer, S., Koch, R., Metzger, J.O., (2003) Angew. Chem., Int. Ed, 42, p. 4700
dc.descriptionSantos, L.S., Metzger, J.O., (2006) Angew. Chem., Int. Ed, 45, p. 977
dc.descriptionSantos, L.S., Knaack, L., Metzger, J.O., (2005) Int. J. Mass Spectrom, 246, p. 84
dc.descriptionSantos, L.S., Pavam, C.H., Almeida, W.P., Coelho, F., Eberlin, M.N., (2004) Angew. Chem, 116, p. 4430
dc.descriptionAngew, (2004) Chem., Int. Ed, 43, p. 4330
dc.descriptionDomingos, J.B., Longhinotti, E., Brandao, T.A.S., Bunton, C.A., Santos, L.S., Eberlin, M.N., Nome, F., (2004) J. Org. Chem, 69, p. 6024
dc.descriptionMeurer, E.C., Santos, L.S., Pilli, R.A., Eberlin, M.N., (2003) Org. Lett, 5, p. 1391
dc.descriptionSabino, A.A., Machado, A.H.L., Correia, C.R.D., Eberlin, M.N., (2004) Angew. Chem, 116, p. 2568
dc.descriptionAngew, (2004) Chem., Int. Ed, 43, p. 2514
dc.descriptionHilderling, C., Adlhart, C., Chen, P., (1998) Angew. Chem, 110, p. 2831
dc.descriptionAngew, (1998) Chem., Int. Ed, 37, p. 2685
dc.descriptionChen, P., (2003) Angew. Chem, 115, p. 2938
dc.descriptionAngew, (2003) Chem., Int. Ed, 42, p. 2832
dc.descriptionRaminelli, C., Prechtl, M.H.G., Santos, L.S., Eberlin, M.N., Comasseto, J.V., (2004) Organometallics, 23, p. 3990
dc.descriptionDomingos, J.B., Longhinotti, E., Brandao, T.A.S., Santos, L.S., Eberlin, M.N., Bunton, C.A., Nome, F., (2004) J. Org. Chem, 69, p. 7898
dc.descriptionWhitehouse, C.M., Dreyer, R.N., Yamashita, M., Fenn, J.B., (1985) Anal. Chem, 57, p. 675
dc.descriptionFenn, J.B., Mann, M., Meng, C.K., Wong, S.F., Whitehouse, C.M., (1989) Science, 246, p. 64
dc.descriptionde la Mora, J.F., Van Berckel, G.J., Enke, C.G., Cole, R.B., Martinez-Sanchez, M., Fenn, J.B., (2000) J. Mass Spectrom, 35, p. 939
dc.descriptionCerchiaro, G., Saboya, P.L., Ferreira, A.M.C., Tomazela, D.M., Eberlin, M.N., (2004) Transition Met. Chem, 29, p. 495
dc.descriptionTomazela, D.M., Sabino, A.A., Sparrapan, R., Gozzo, F.C., Eberlin, M.N., (2006) J. Am. Soc. Mass Spectrom, 17, p. 1014
dc.descriptionSantos, L.S., Padilha, M.C., Neto, F.R.D., Pereira, A.D., Menegatti, R., Fraga, C.A.M., Barreiro, E.B., Eberlin, M.N., (2005) J. Mass Spectrom, 40, p. 815. , For an example concerning similar dissociation patterns, see
dc.languageen
dc.publisher
dc.relationJournal of Organic Chemistry
dc.rightsfechado
dc.sourceScopus
dc.titleThe Mechanism Of Tröger's Base Formation Probed By Electrospray Ionization Mass Spectrometry
dc.typeArtículos de revistas


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