메뉴 건너뛰기




Volumn 46, Issue 9, 2011, Pages 856-858

ESI-MS study on transient intermediates in the fast cyclopropenium- activated chlorination reaction of alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; CYCLOPROPANE DERIVATIVE; CYCLOPROPENIUM; UNCLASSIFIED DRUG;

EID: 80052817473     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1960     Document Type: Letter
Times cited : (9)

References (33)
  • 1
    • 70349628874 scopus 로고    scopus 로고
    • Aromatic cation activation of alcohols: Conversion to alkyl chlorides using dichlorodiphenylcyclopropene
    • B. D. Kelly, T. H. Lambert,. Aromatic cation activation of alcohols: conversion to alkyl chlorides using dichlorodiphenylcyclopropene. J. Am. Chem. Soc. 2009, 131, 13930.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 13930
    • Kelly, B.D.1    Lambert, T.H.2
  • 2
    • 77950792877 scopus 로고    scopus 로고
    • Nucleophilic acyl substitution via aromatic cation activation of carboxylic acids: Rapid generation of acid chlorides under mild conditions
    • D. J. Hardee, L. Kovalchuke, T. Lambert,. Nucleophilic acyl substitution via aromatic cation activation of carboxylic acids: rapid generation of acid chlorides under mild conditions. J. Am. Chem. Soc. 2010, 132, 5002.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 5002
    • Hardee, D.J.1    Kovalchuke, L.2    Lambert, T.3
  • 3
    • 77955213939 scopus 로고    scopus 로고
    • Cyclopropenium ion catalysed Beckmann rearrangement
    • V. P. Srivastava, R. P. Garima, L. D. S. Yadav,. Cyclopropenium ion catalysed Beckmann rearrangement. Chem. Commun. 2010, 46, 5808.
    • (2010) Chem. Commun. , vol.46 , pp. 5808
    • Srivastava, V.P.1    Garima, R.P.2    Yadav, L.D.S.3
  • 4
    • 79951630781 scopus 로고    scopus 로고
    • Cyclopropenium-activated Beckmann rearrangement. Catalysis versus self-propagation in reported organocatalytic Beckmann rearrangements
    • C. M. Vanos, T. H. Lambert,. Cyclopropenium-activated Beckmann rearrangement. Catalysis versus self-propagation in reported organocatalytic Beckmann rearrangements. Chem. Sci. 2010, 1, 705.
    • (2010) Chem. Sci. , vol.1 , pp. 705
    • Vanos, C.M.1    Lambert, T.H.2
  • 5
    • 79951599208 scopus 로고    scopus 로고
    • Cyclopropenium-activated cyclodehydration of diols
    • B. D. Kelly, T. H. Lambert,. Cyclopropenium-activated cyclodehydration of diols. Org. Lett. 2011, 13, 740.
    • (2011) Org. Lett. , vol.13 , pp. 740
    • Kelly, B.D.1    Lambert, T.H.2
  • 6
    • 0038559706 scopus 로고
    • Synthesis of the s-triphenylcyclopropenyl cation
    • R. Breslow,. Synthesis of the s-triphenylcyclopropenyl cation. J. Am. Chem. Soc. 1957, 79, 5318.
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 5318
    • Breslow, R.1
  • 7
    • 0001220337 scopus 로고
    • The sym-triphenylcyclopropenyl cation, a novel aromatic system
    • R. Breslow, C. Yuan,. The sym-triphenylcyclopropenyl cation, a novel aromatic system. J. Am. Chem. Soc. 1958, 80, 5991.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 5991
    • Breslow, R.1    Yuan, C.2
  • 8
    • 0000539604 scopus 로고
    • Chlorocyclopropenes, chlorocyclopropenyl cations, and cyclopropenone
    • R. Breslow, G. Ryan, J. T. Groves,. Chlorocyclopropenes, chlorocyclopropenyl cations, and cyclopropenone. J. Am. Chem. Soc. 1970, 92, 988.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 988
    • Breslow, R.1    Ryan, G.2    Groves, J.T.3
  • 9
    • 0001689963 scopus 로고
    • A modification of the Hueckel rule. Effective discontinuity of cyclic conjugation
    • S. Inagaki, Y. Hirabayashi,. A modification of the Hueckel rule. Effective discontinuity of cyclic conjugation. J. Am. Chem. Soc. 1977, 99, 7418.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 7418
    • Inagaki, S.1    Hirabayashi, Y.2
  • 10
    • 0038640173 scopus 로고    scopus 로고
    • Cyclopropenylium cations, cyclopropenones, and heteroanalogues recent advances
    • K. Komatsu, T. Kitagawa,. Cyclopropenylium cations, cyclopropenones, and heteroanalogues recent advances. Chem. Rev. 2003, 103, 1371.
    • (2003) Chem. Rev. , vol.103 , pp. 1371
    • Komatsu, K.1    Kitagawa, T.2
  • 12
    • 34250740975 scopus 로고    scopus 로고
    • Electrospray ionization mass spectrometry: A major tool to investigate reaction mechanisms in both solution and the gas phase
    • M. N. Eberlin,. Electrospray ionization mass spectrometry: a major tool to investigate reaction mechanisms in both solution and the gas phase. Eur. J. Mass Spectrom. 2007, 13, 19.
    • (2007) Eur. J. Mass Spectrom. , vol.13 , pp. 19
    • Eberlin, M.N.1
  • 13
    • 38349097338 scopus 로고    scopus 로고
    • Online mechanistic investigations of catalyzed reactions by electrospray ionization mass spectrometry: A tool to intercept transient species in solution
    • L. S. Santos,. Online mechanistic investigations of catalyzed reactions by electrospray ionization mass spectrometry: a tool to intercept transient species in solution. Eur. J. Org. Chem. 2008, 2008, 235.
    • (2008) Eur. J. Org. Chem. , vol.2008 , pp. 235
    • Santos, L.S.1
  • 14
    • 44349137015 scopus 로고    scopus 로고
    • Electrospray ionization mass spectrometric studies on intermediates of organic reaction
    • L. Zhang, R. Qian, X. Zhang, J. Zhou, Y. L. Guo,. Electrospray ionization mass spectrometric studies on intermediates of organic reaction. Chin. J. Org. Chem. 2008, 28, 372.
    • (2008) Chin. J. Org. Chem. , vol.28 , pp. 372
    • Zhang, L.1    Qian, R.2    Zhang, X.3    Zhou, J.4    Guo, Y.L.5
  • 16
    • 77955403181 scopus 로고    scopus 로고
    • Gas-phase synthesis of hydro-diphenylcyclopropenylium via nonclassical Favorskii rearrangement from alkali-cationized α,α′- dibromodibenzyl ketone
    • Z. X. Zhao, H. Y. Wang, C. Xu, Y. L. Guo,. Gas-phase synthesis of hydro-diphenylcyclopropenylium via nonclassical Favorskii rearrangement from alkali-cationized α,α′-dibromodibenzyl ketone. Rapid Commun. Mass Spectrom. 2010, 24, 2665.
    • (2010) Rapid Commun. Mass Spectrom. , vol.24 , pp. 2665
    • Zhao, Z.X.1    Wang, H.Y.2    Xu, C.3    Guo, Y.L.4
  • 17
    • 0037008561 scopus 로고    scopus 로고
    • Investigation of reactive intermediates of chemical reactions in solution by electrospray ionization mass spectrometry: Radical chain reactions
    • J. Griep-Raming, S. Meyer, T. Bruhn, J. O. Metzger,. Investigation of reactive intermediates of chemical reactions in solution by electrospray ionization mass spectrometry: radical chain reactions. Angew. Chem. Int. Ed. 2002, 41, 2738.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2738
    • Griep-Raming, J.1    Meyer, S.2    Bruhn, T.3    Metzger, J.O.4
  • 18
    • 0142119330 scopus 로고    scopus 로고
    • Investigation of reactive intermediates of chemical reactions in solution by electrospray ionization mass spectrometry: Radical cation chain reactions
    • S. Meyer, R. Koch, J. O. Metzger,. Investigation of reactive intermediates of chemical reactions in solution by electrospray ionization mass spectrometry: radical cation chain reactions. Angew. Chem. Int. Ed. 2003, 42, 4700.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 4700
    • Meyer, S.1    Koch, R.2    Metzger, J.O.3
  • 19
    • 7744230919 scopus 로고    scopus 로고
    • Detection of transient radical cations in electron transfer-initiated Diels-Alder reactions by electrospray ionization mass spectrometry
    • S. Furmeier, J. O. Metzger,. Detection of transient radical cations in electron transfer-initiated Diels-Alder reactions by electrospray ionization mass spectrometry. J. Am. Chem. Soc. 2004, 126, 14485.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 14485
    • Furmeier, S.1    Metzger, J.O.2
  • 20
    • 32044437434 scopus 로고    scopus 로고
    • Study of homogeneously catalyzed Ziegler-Natta polymerization of ethene by ESI-MS
    • L. S. Santos, J. Metzger,. Study of homogeneously catalyzed Ziegler-Natta polymerization of ethene by ESI-MS. Angew. Chem. Int. Ed. 2006, 45, 977.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 977
    • Santos, L.S.1    Metzger, J.2
  • 21
    • 34548737141 scopus 로고    scopus 로고
    • Electrospray ionization mass spectrometric study on the direct organocatalytic alpha-halogenation of aldehydes
    • C. A. Marquez, F. Fabbretti, J. O. Metzger,. Electrospray ionization mass spectrometric study on the direct organocatalytic alpha-halogenation of aldehydes. Angew. Chem. Int. Ed. 2007, 46, 6915.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 6915
    • Marquez, C.A.1    Fabbretti, F.2    Metzger, J.O.3
  • 22
    • 41149109462 scopus 로고    scopus 로고
    • On-line monitoring of Brookhart polymerization by electrospray ionization mass spectrometry
    • L. S. Santos, J. O. Metzger,. On-line monitoring of Brookhart polymerization by electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 2008, 22, 898.
    • (2008) Rapid Commun. Mass Spectrom. , vol.22 , pp. 898
    • Santos, L.S.1    Metzger, J.O.2
  • 23
    • 47249091899 scopus 로고    scopus 로고
    • ESI-MS study on first-generation ruthenium olefin metathesis catalysts in solution: Direct detection of the catalytically active 14-electron ruthenium intermediate
    • H. Y. Wang, J. O. Metzger,. ESI-MS study on first-generation ruthenium olefin metathesis catalysts in solution: direct detection of the catalytically active 14-electron ruthenium intermediate. Organometallics 2008, 27, 2761.
    • (2008) Organometallics , vol.27 , pp. 2761
    • Wang, H.Y.1    Metzger, J.O.2
  • 25
    • 70350218752 scopus 로고    scopus 로고
    • ESIMS studies and calculations on alkali-metal adduct ions of ruthenium olefin metathesis catalysts and their catalytic activity in metathesis reactions
    • H. Y. Wang, W. L. Yim, T. Klüner, J. O. Metzger,. ESIMS studies and calculations on alkali-metal adduct ions of ruthenium olefin metathesis catalysts and their catalytic activity in metathesis reactions. Chem. Eur. J. 2009, 15, 10948.
    • (2009) Chem. Eur. J. , vol.15 , pp. 10948
    • Wang, H.Y.1    Yim, W.L.2    Klüner, T.3    Metzger, J.O.4
  • 26
    • 77749242800 scopus 로고    scopus 로고
    • Monitoring self-sorting by electrospray ionization mass spectrometry: Formation intermediates and error-correction during the self-assembly of multiply threaded pseudorotaxanes
    • W. Jiang, A. Schafer, P. Mohr, C. A. Schalley,. Monitoring self-sorting by electrospray ionization mass spectrometry: formation intermediates and error-correction during the self-assembly of multiply threaded pseudorotaxanes. J. Am. Chem. Soc. 2010, 132, 2309.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 2309
    • Jiang, W.1    Schafer, A.2    Mohr, P.3    Schalley, C.A.4
  • 27
    • 5644249240 scopus 로고    scopus 로고
    • Mass spectrometry sampling under ambient conditions with desorption electrospray ionization
    • Z. Takats, J. M. Wiseman, B. Gologan, R. G. Cooks,. Mass spectrometry sampling under ambient conditions with desorption electrospray ionization. Science 2004, 306, 471.
    • (2004) Science , vol.306 , pp. 471
    • Takats, Z.1    Wiseman, J.M.2    Gologan, B.3    Cooks, R.G.4
  • 28
    • 27544464685 scopus 로고    scopus 로고
    • Desorption electrospray ionization of explosives on surfaces: Sensitivity and selectivity enhancement by reactive desorption electrospray ionization
    • I. Cotte-Rodriguez, Z. Takats, N. Talaty, H. W. Chen, R. G. Cooks,. Desorption electrospray ionization of explosives on surfaces: sensitivity and selectivity enhancement by reactive desorption electrospray ionization. Anal. Chem. 2005, 77, 6755.
    • (2005) Anal. Chem. , vol.77 , pp. 6755
    • Cotte-Rodriguez, I.1    Takats, Z.2    Talaty, N.3    Chen, H.W.4    Cooks, R.G.5
  • 29
    • 33845533193 scopus 로고    scopus 로고
    • Droplet dynamics and ionization mechanisms in desorption electrospray ionization mass spectrometry
    • A. Venter, P. E. Sojka, R. G. Cooks,. Droplet dynamics and ionization mechanisms in desorption electrospray ionization mass spectrometry. Anal. Chem. 2006, 78, 8549.
    • (2006) Anal. Chem. , vol.78 , pp. 8549
    • Venter, A.1    Sojka, P.E.2    Cooks, R.G.3
  • 30
    • 33646584508 scopus 로고    scopus 로고
    • Extractive electrospray ionization for direct analysis of undiluted urine, milk and other complex mixtures without sample preparation
    • H. Chen, A. Venter, R. G. Cooks,. Extractive electrospray ionization for direct analysis of undiluted urine, milk and other complex mixtures without sample preparation. Chem. Commun. 2006, 19, 2042.
    • (2006) Chem. Commun. , vol.19 , pp. 2042
    • Chen, H.1    Venter, A.2    Cooks, R.G.3
  • 32
    • 67849132894 scopus 로고    scopus 로고
    • Electron-transfer-catalyzed dimerization of trans-anethole: Detection of the distonic tetramethylene radical cation intermediate by extractive electrospray ionization mass spectrometry
    • C. A. Marquez, H. Y. Wang, F. Fabbretti, J. O. Metzger,. Electron-transfer-catalyzed dimerization of trans-anethole: detection of the distonic tetramethylene radical cation intermediate by extractive electrospray ionization mass spectrometry. J. Am. Chem. Soc. 2008, 130, 17208.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 17208
    • Marquez, C.A.1    Wang, H.Y.2    Fabbretti, F.3    Metzger, J.O.4
  • 33
    • 78650713170 scopus 로고    scopus 로고
    • Detecting reaction intermediates in liquids on the millisecond time scale using desorption electrospray ionization
    • R. H. Perry, M. Splendore, A. Chien, N. K. Davis, R. N. Zare,. Detecting reaction intermediates in liquids on the millisecond time scale using desorption electrospray ionization. Angew. Chem. Int. Ed. 2011, 50, 250.
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 250
    • Perry, R.H.1    Splendore, M.2    Chien, A.3    Davis, N.K.4    Zare, R.N.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.