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Volumn 22, Issue 3, 2011, Pages 557-567

Mass spectrometry studies of the retro-cycloaddition reaction of pyrrolidino and 2-pyrazolinofullerene derivatives under negative esi conditions

Author keywords

ESI; Pyrazolinofullerenes; Pyrrolidinofullerenes; Retrocycloaddition reaction

Indexed keywords

[60] FULLERENE; CARBON AND NITROGEN; ELECTROCHEMICAL PROCESS; ESI; FRAGMENTATION PATHWAYS; HETEROCYCLIC RINGS; MALDI-MASS SPECTROMETRY; MASS SPECTRAL FRAGMENTATION; NITROGEN ATOM; PYRAZOLINOFULLERENES; PYRROLIDINOFULLERENES; RETROCYCLOADDITION;

EID: 79955765283     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-010-0063-y     Document Type: Article
Times cited : (16)

References (48)
  • 2
    • 33744905790 scopus 로고    scopus 로고
    • New challenges in fullerene chemistry
    • DOI 10.1039/b601582b
    • Martín, N.: New challenges in fullerene chemistry. Chem. Commun. 2093-2104 (2006) (Pubitemid 43844068)
    • (2006) Chemical Communications , Issue.20 , pp. 2093-2104
    • Martin, N.1
  • 4
    • 66249086921 scopus 로고    scopus 로고
    • Ordering fullerenes at the nanometer scale on solid surfaces
    • Sánchez, L., Otero, R., Gallego, J.M., Miranda, R., Martín, N.: Ordering fullerenes at the nanometer scale on solid surfaces. Chem. Rev. 109, 2081-2091 (2009)
    • (2009) Chem. Rev. , vol.109 , pp. 2081-2091
    • Sánchez, L.1    Otero, R.2    Gallego, J.M.3    Miranda, R.4    Martín, N.5
  • 8
    • 57449110193 scopus 로고    scopus 로고
    • Mass Spectrometry across the sciences
    • McLafferty, F.W.: Mass Spectrometry across the sciences. Proc. Natl Acad. Sci. USA 105, 18088-18089 (2008)
    • (2008) Proc. Natl Acad. Sci. USA , vol.105 , pp. 18088-18089
    • McLafferty, F.W.1
  • 10
    • 0037397065 scopus 로고    scopus 로고
    • 60 primary ion beam system for time of flight secondary ion mass spectrometry: Its development and secondary ion yield characteristics
    • DOI 10.1021/ac026338o
    • 60 primary ion beam system for time of flight secondary ion mass spectrometry: Its development and secondary ion yield characteristics. Anal. Chem. 75, 1754-1764 (2003) (Pubitemid 36512619)
    • (2003) Analytical Chemistry , vol.75 , Issue.7 , pp. 1754-1764
    • Weibel, D.1    Wong, S.2    Lockyer, N.3    Blenkinsopp, P.4    Hill, R.5    Vickerman, J.C.6
  • 12
    • 77951710536 scopus 로고    scopus 로고
    • Laser desorption/ionization mass spectrometry analysis of small molecules using fullerene-derivatized silica as energy-absorbing material
    • Zoltan, S., Vallant, R.M., Takatsy, A., Bakry, R., Najam-ul-Haq, M., Matthias, R., Huck, C., Bonn, Günther, K.: Laser desorption/ionization mass spectrometry analysis of small molecules using fullerene-derivatized silica as energy-absorbing material. J. Mass Spectrom. 45, 545-552 (2010)
    • (2010) J. Mass Spectrom. , vol.45 , pp. 545-552
    • Zoltan, S.1    Vallant, R.M.2    Takatsy, A.3    Bakry, R.4    Najam-ul-Haq, M.5    Matthias, R.6    Huck, C.7    Bonn Günther, K.8
  • 14
    • 0034743060 scopus 로고    scopus 로고
    • Some 4-fluorophenyl derivatives of [60]fullerene; spontaneous oxidation and oxide-induced fragmentation to C58
    • Darwish, A.D., Avent, A.G., Birkett, P.R., Kroto, H.W., Taylor, R., Walton, D.R.M.: Some 4-fluorophenyl derivatives of [60]fullerene; spontaneous oxidation and oxide-induced fragmentation to C58. J. Chem. Soc. Perkin Trans 2, 2351-2357 (2001)
    • (2001) J. Chem. Soc. Perkin Trans , vol.2 , pp. 2351-2357
    • Darwish, A.D.1    Avent, A.G.2    Birkett, P.R.3    Kroto, H.W.4    Taylor, R.5    Walton, D.R.M.6
  • 16
    • 1842480412 scopus 로고    scopus 로고
    • Novel experimental arrangement developed for direct fullerene analysis by electrospray time-of-flight mass spectrometry
    • Kozlovski, V., Brusov, V., Sulimenkov, I., Pikhtelev, A., Dodonov, A.: Novel experimental arrangement developed for direct fullerene analysis by electrospray time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 18, 780-786 (2004) (Pubitemid 38451023)
    • (2004) Rapid Communications in Mass Spectrometry , vol.18 , Issue.7 , pp. 780-786
    • Kozlovski, V.1    Brusov, V.2    Sulimenkov, I.3    Pikhtelev, A.4    Dodonov, A.5
  • 17
    • 0000450167 scopus 로고    scopus 로고
    • O-Quinodimethanes: Efficient intermediates in organic synthesis
    • Segura, J.L., Martín, N.: O-Quinodimethanes: Efficient intermediates in organic synthesis. Chem. Rev. 99, 3199-3246 (1999) (Pubitemid 129583052)
    • (1999) Chemical Reviews , vol.99 , Issue.11 , pp. 3199-3246
    • Segura, J.L.1    Martin, N.2
  • 18
    • 0042969882 scopus 로고    scopus 로고
    • Thermal and microwave-assisted synthesis of Diels-Alder adducts of [60]fullerene with 2, 3-pyrazinoquinodimethanes: Characterization and electrochemical properties
    • Fernández-Paniagua, U.M., Illescas, B., Martín, M., Seoane, C., de la Cruz, P., de la Hoz, A., Langa, F.: Thermal and microwave-assisted synthesis of Diels-Alder adducts of [60]fullerene with 2, 3- pyrazinoquinodimethanes: Characterization and electrochemical properties. J. Org. Chem. 62, 3705-3710 (1997) (Pubitemid 127492976)
    • (1997) Journal of Organic Chemistry , vol.62 , Issue.11 , pp. 3705-3710
    • Fernandez-Paniagua, U.M.1    Illescas, B.2    Martin, N.3    Seoane, C.4    De La Cruz, P.5    De La Hoz, A.6    Langa, F.7
  • 19
    • 0034595627 scopus 로고    scopus 로고
    • The syntheses of pyrazino-containing sultines and their application in Diels-Alder reactions with electron-poor olefins and [60]fullerene
    • DOI 10.1021/jo9918448
    • Liu, J.-H., Wu, A.-T., Huang, M.-H., Wu, C.-W., Cheng, W.-S.: The synthesis of pyrazino-containing sultines and their applications in Diels-Alder reactions with electron poor olefins and [60]fullerene. J. Org. Chem. 65, 3395-3403 (2000) (Pubitemid 30346793)
    • (2000) Journal of Organic Chemistry , vol.65 , Issue.11 , pp. 3395-3403
    • Liu, J.-H.1    Wu, A.-T.2    Huang, M.-H.3    Wu, C.-W.4    Chung, W.-S.5
  • 21
    • 12344328451 scopus 로고    scopus 로고
    • Synthesis of [60]fullerene-based α-amino acid derivatives
    • DOI 10.1016/j.tet.2004.12.007, PII S0040402004020204
    • Enes, R.F., Tom?, A.C., Cavaleiro, J.A.S.: Synthesis of [60]fullerenebased a-amino acid derivatives. Tetrahedron 61, 1423-1431 (2005) (Pubitemid 40139135)
    • (2005) Tetrahedron , vol.61 , Issue.6 , pp. 1423-1431
    • Enes, R.F.1    Tome, A.C.2    Cavaleiro, J.A.S.3
  • 22
    • 0001213412 scopus 로고    scopus 로고
    • Fulleropyrrolidines: A family of full-fledged fullerene derivatives
    • Prato, M., Maggini, M.: Fulleropyrrolidines: A family of full-fledged fullerene derivatives. Acc. Chem. Res. 31, 519-526 (1998) (Pubitemid 128473644)
    • (1998) Accounts of Chemical Research , vol.31 , Issue.9 , pp. 519-526
    • Prato, M.1    Maggini, M.2
  • 23
    • 0038633251 scopus 로고    scopus 로고
    • The addition of azomethine ylides to [60]fullerene leading to fulleropyrrolidines
    • Tagmatarchis, N., Prato. M.: The addition of azomethine ylides to [60] fullerene leading to fulleropyrrolidines. Synlett 768-779 (2003) (Pubitemid 36577752)
    • (2003) Synlett , Issue.6 , pp. 768-779
    • Tagmatarchis, N.1    Prato, M.2
  • 24
    • 42149195095 scopus 로고    scopus 로고
    • On the thermal stability of [60]fullerene cycloadducts: Retro-cycloaddition reaction of 2-pyrazolino[4,5:1,2][60]fullerenes
    • DOI 10.1021/jo702741n
    • Delgado, J.L., Oswald, F., Cardinali, F., Langa, F., Martín, N.: On the thermal stability of [60]fullerene cycloadducts: Retro-cycloaddition reaction of 2-pyrazolino[4, 5:1, 2] [60]fullerene. J. Org. Chem. 73, 3184-3188 (2008) (Pubitemid 351543969)
    • (2008) Journal of Organic Chemistry , vol.73 , Issue.8 , pp. 3184-3188
    • Delgado, J.L.1    Oswald, F.2    Cardinali, F.3    Langa, F.4    Martin, N.5
  • 26
    • 84986791344 scopus 로고
    • Retro-Diels-Alder reaction in mass spectrometry
    • Turecek, F., Hanu, V.: Retro-Diels-Alder reaction in mass spectrometry. Mass Spectrom. Rev. 3, 85-152 (1984)
    • (1984) Mass Spectrom. Rev. , vol.3 , pp. 85-152
    • Turecek, F.1    Hanu, V.2
  • 27
    • 0035563743 scopus 로고    scopus 로고
    • Mass-spectrometric differentiation of diexo- and diendo-fused isomers of norbornane/ene-condensed 2-thiouracil and 1,3-thiazino[3,2-a]pyrimidine derivatives: Stereoselectivity of retro-diels-alder fragmentations under EI and CI conditions
    • DOI 10.1016/S1044-0305(01)00280-X, PII S104403050100280X
    • Ovcharenko, V.V., Shaikhutdinov, R.A., Pihlaja, K.: Mass-spectrometric differentiation of diexo-and diendo-fused isomers of norbornane/ene condensed 2-thiouracil and 1, 3-thiazino[3, 2-a]-pyrimidine derivatives: Stereoselectivity of retro-Diels-Alder fragmentation under EI and CI conditions. J. Am. Soc. Mass Spectrom. 12, 1011-1019 (2001) (Pubitemid 34552664)
    • (2001) Journal of the American Society for Mass Spectrometry , vol.12 , Issue.9 , pp. 1011-1019
    • Ovcharenko, V.V.1    Shaikhutdinov, R.A.2    Pihlaja, K.3    Stajer, G.4
  • 28
    • 32144452098 scopus 로고    scopus 로고
    • Retro-Diels-Alder and other electron ionization-induced fragmentation reactions of 1 2 3, 4-tetrahydrobenzopyran-2, 3-dicarboxylic acid derivatives
    • Szmigielski, R., Danikiewicz, W., Dolatowska, K., Wojciechowski, K.: Retro-Diels-Alder and other electron ionization-induced fragmentation reactions of 1, 2, 3, 4-tetrahydrobenzopyran-2, 3-dicarboxylic acid derivatives. Int. J. Mass Spectrom. 248, 148-154 (2006)
    • (2006) Int. J. Mass Spectrom. , vol.248 , pp. 148-154
    • Szmigielski, R.1    Danikiewicz, W.2    Dolatowska, K.3    Wojciechowski, K.4
  • 31
    • 17844373011 scopus 로고    scopus 로고
    • [60]Fullerene adducts with 9-substituted anthracenes: Mechanochemical preparation and retro Diels-Alder reaction
    • DOI 10.1016/j.tet.2005.02.089
    • Wang, G.-W., Chen, Z.-X., Murata, Y., Komatsu, K.: [60]Fullerene adducts with 9-substituted anthracenes: Mechanochemical preparation and retro Diels-Alder reaction. Tetrahedron 61, 4851-4856 (2005) (Pubitemid 40591612)
    • (2005) Tetrahedron , vol.61 , Issue.20 , pp. 4851-4856
    • Wang, G.-W.1    Chen, Z.-X.2    Murata, Y.3    Komatsu, K.4
  • 33
    • 66949126053 scopus 로고    scopus 로고
    • Pyrimidine ortho-quinodimethanes. Part 2: Synthesis of new [60]fullerene adducts base on substituted pyrimidine derivatives and their 1H NMR dynamic study
    • Herrera, A., Martínez-Alvarez, R., Martín, N., Chioua, M., Chioua, R., Molero, D., Sánchez-Vázquez, A., Almy, J.: Pyrimidine ortho-quinodimethanes. Part 2: Synthesis of new [60]fullerene adducts base on substituted pyrimidine derivatives and their 1H NMR dynamic study. Tetrahedron 65, 5817-5823 (2009)
    • (2009) Tetrahedron , vol.65 , pp. 5817-5823
    • Herrera, A.1    Martínez-Alvarez, R.2    Martín, N.3    Chioua, M.4    Chioua, R.5    Molero, D.6    Sánchez-Vázquez, A.7    Almy, J.8
  • 35
    • 61349129082 scopus 로고    scopus 로고
    • Oxidation of 3-alkyl-substituted 2-pyrazolino[60]fullerenes: A new formyl-containing building block for fullerene chemistry
    • Delgado, J.L., Cardinali, F., Espíldora, E., Torres, M.R., Langa, F., Martín, N.: Oxidation of 3-alkyl-substituted 2-pyrazolino[60] fullerenes: A new formyl-containing building block for fullerene chemistry. Org. Lett. 17, 3705-3708 (2008)
    • (2008) Org. Lett. , vol.17 , pp. 3705-3708
    • Delgado, J.L.1    Cardinali, F.2    Espíldora, E.3    Torres, M.R.4    Langa, F.5    Martín, N.6
  • 38
    • 70349558255 scopus 로고    scopus 로고
    • An efficient approach to chiral fullerene derivatives by catalytic enantioselective 1, 3-dipolar cycloadditions
    • Filippone, S., Maroto, E.E., Martín-Domenech, A., Suárez, M., Martín, N.: An efficient approach to chiral fullerene derivatives by catalytic enantioselective 1, 3-dipolar cycloadditions. Nat. Chem. 1, 578-582 (2009)
    • (2009) Nat. Chem. , vol.1 , pp. 578-582
    • Filippone, S.1    Maroto, E.E.2    Martín-Domenech, A.3    Suárez, M.4    Martín, N.5
  • 39
    • 72449156588 scopus 로고    scopus 로고
    • Direct observation of a photoinduced nonstabilized nitrile imine structure in the solid state
    • Zheng, S.-L., Wang, Y., Yu, Z., Lin, Q., Coppens, P.: Direct observation of a photoinduced nonstabilized nitrile imine structure in the solid state. J. Am. Chem. Soc. 131, 18036-18037 (2009)
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 18036-18037
    • Zheng, S.-L.1    Wang, Y.2    Yu, Z.3    Lin, Q.4    Coppens, P.5
  • 41
    • 0030082956 scopus 로고    scopus 로고
    • 60 cycloadducts - Synthesis and mass spectrometric characterization
    • DOI 10.1016/0379-6779(96)80066-X
    • 60 cycloadducts-synthesis and mass spectrometry characterization. Synth. Met. 77, 93-95 (1996) (Pubitemid 126341296)
    • (1996) Synthetic Metals , vol.77 , Issue.1-3 , pp. 93-95
    • Bartoszek, M.1    Duczek, W.2    Tittelbach, F.3    Niclas, H.-J.4
  • 42
    • 0142165255 scopus 로고    scopus 로고
    • Synthesis and study of novel fulleropyrrolidines bearing biologically active 1,4-dihydropyridines
    • DOI 10.1016/j.tet.2003.09.047
    • Suárez, M., Verdecia, Y., Illescas, B., Martínez-Alvarez, R., Alvarez, A., Ochoa, E., Seoane, C., Kayali, N., Martín, N.: Synthesis and study of novel fulleropyrrolidines bearing biologically active 1, 4-dihydropyridines. Tetrahedron 59, 9179-9186 (2003) (Pubitemid 37329567)
    • (2003) Tetrahedron , vol.59 , Issue.46 , pp. 9179-9186
    • Suarez, M.1    Verdecia, Y.2    Illescas, B.3    Martinez-Alvarez, R.4    Alvarez, A.5    Ochoa, E.6    Seoane, C.7    Kayali, N.8    Martin, N.9
  • 43
    • 0043204453 scopus 로고    scopus 로고
    • Synthesis of water soluble fulleropyrrolidines bearing biologically active arylpiperazines
    • DOI 10.1016/S0040-4020(03)01017-2
    • Illescas, B.M., Martínez-Alvarez, R., Fernández-Gadea, J., Martín, N.: Synthesis of water soluble fulleropyrrolidines bearing biologically active piperazines. Tetrahedron 59, 6569-6577 (2003) (Pubitemid 36930143)
    • (2003) Tetrahedron , vol.59 , Issue.34 , pp. 6569-6577
    • Illescas, B.M.1    Martinez-Alvarez, R.2    Fernandez-Gadea, J.3    Martin, N.4
  • 44
    • 0001396269 scopus 로고
    • Cyclopropanation of fullerenes
    • Bingel, C.: Cyclopropanation of fullerenes. Chem. Ber. 126, 1957-1959 (1993)
    • (1993) . Chem. Ber. , vol.126 , pp. 1957-1959
    • Bingel, C.1


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