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Volumn 10, Issue 1, 2011, Pages 123-127

Cationic and radical intermediates in the acid photorelease from aryl sulfonates and phosphates

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EID: 78650758061     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c0pp00284d     Document Type: Article
Times cited : (29)

References (45)
  • 1
    • 40149095239 scopus 로고    scopus 로고
    • Chemistry of photolithographic imaging materials based on the chemical amplification concept
    • S.-Y. Moon J.-M. Kim Chemistry of photolithographic imaging materials based on the chemical amplification concept J. Photochem. Photobiol. C 2007 8 157 173
    • (2007) J. Photochem. Photobiol. C , vol.8 , pp. 157-173
    • Moon, S.-Y.1    Kim, J.-M.2
  • 2
    • 0000296299 scopus 로고
    • The photogeneration of acid and base within polymer coatings: Approaches to polymer curing and imaging
    • J. M. Frechét The photogeneration of acid and base within polymer coatings: Approaches to polymer curing and imaging Pure Appl. Chem. 1992 64 1239 1248
    • (1992) Pure Appl. Chem. , vol.64 , pp. 1239-1248
    • Frechét, J.M.1
  • 3
    • 0029771739 scopus 로고    scopus 로고
    • Photoacid and photobase generators: Chemistry and applications to polymeric materials
    • M. Shirai M. Tsunooka Photoacid and photobase generators: Chemistry and applications to polymeric materials Prog. Polym. Sci. 1996 21 1 45
    • (1996) Prog. Polym. Sci. , vol.21 , pp. 1-45
    • Shirai, M.1    Tsunooka, M.2
  • 4
    • 0037471648 scopus 로고    scopus 로고
    • Novel photoacid generators for photodirected oligonucleotide synthesis
    • P. J. Serafinowski P. B. Garland Novel photoacid generators for photodirected oligonucleotide synthesis J. Am. Chem. Soc. 2003 125 962 965
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 962-965
    • Serafinowski, P.J.1    Garland, P.B.2
  • 5
    • 1842683164 scopus 로고    scopus 로고
    • In situ synthesis of oligonucleotide microarrays
    • X. Gao E. Gulari X. Zhou In situ synthesis of oligonucleotide microarrays Biopolymers 2004 73 579 596
    • (2004) Biopolymers , vol.73 , pp. 579-596
    • Gao, X.1    Gulari, E.2    Zhou, X.3
  • 6
    • 0033364922 scopus 로고    scopus 로고
    • The discovery and development of onium salt cationic photoinitiators
    • J. V. Crivello The discovery and development of onium salt cationic photoinitiators J. Polym. Sci., Part A: Polym. Chem. 1999 37 4241 4254
    • (1999) J. Polym. Sci., Part A: Polym. Chem. , vol.37 , pp. 4241-4254
    • Crivello, J.V.1
  • 8
    • 0025030035 scopus 로고
    • Photochemistry of irgasan-triflate: A simple conversion of an aromatic hydroxyl group to chlorine in the synthesis of polychlorinated diphenyl ethers and polychlorinated dibenzofurans
    • Y.-S. Chang J.-S. Jang M.-L. Deinzer Photochemistry of irgasan-triflate: A simple conversion of an aromatic hydroxyl group to chlorine in the synthesis of polychlorinated diphenyl ethers and polychlorinated dibenzofurans Tetrahedron 1990 46 4161 4164
    • (1990) Tetrahedron , vol.46 , pp. 4161-4164
    • Chang, Y.-S.1    Jang, J.-S.2    Deinzer, M.-L.3
  • 9
    • 84989040654 scopus 로고
    • Acid formation from various sulfonates in a chemical amplification positive resist
    • T. Ueno L. Schlegel N. Hayashi H. Shiraishi T. Iwayanagi Acid formation from various sulfonates in a chemical amplification positive resist Polym. Eng. Sci. 1992 32 1511 1515
    • (1992) Polym. Eng. Sci. , vol.32 , pp. 1511-1515
    • Ueno, T.1    Schlegel, L.2    Hayashi, N.3    Shiraishi, H.4    Iwayanagi, T.5
  • 10
    • 0346367232 scopus 로고
    • Acid formation and deprotection reaction by novel sulfonates in a chemical amplification positive photoresist
    • L. Schlegel T. Ueno H. Shiraishi N. Hayashi T. Iwayanagi Acid formation and deprotection reaction by novel sulfonates in a chemical amplification positive photoresist Chem. Mater. 1990 2 299 305
    • (1990) Chem. Mater. , vol.2 , pp. 299-305
    • Schlegel, L.1    Ueno, T.2    Shiraishi, H.3    Hayashi, N.4    Iwayanagi, T.5
  • 11
    • 0026121518 scopus 로고
    • Highly sensitive positive deep UV resist utilizing a sulfonate acid generator and a tetrahydropyranyl inhibitor
    • DOI 10.1016/0167-9317(91)90042-C, Microcircuit Engineering '90
    • L. Schlegel T. Ueno H. Shiraishi N. Hayashi T. Iwayanagi Highly sensitive positive deep UV resist utilizing a sulfonate acid generator and a tetrahydropyranyl inhibitor Microelectron. Eng. 1991 13 33 36 (Pubitemid 21665511)
    • (1991) Microelectronic Engineering , vol.13 , Issue.1-4 , pp. 33-36
    • Schlegel Leo1    Ueno Takumi2    Shiraishi Hiroshi3    Hayashi Nobuaki4    Iwayanagi Takao5
  • 12
    • 42049098605 scopus 로고    scopus 로고
    • Aryl cation chemistry as an emerging versatile tool for metal-free arylations
    • V. Dichiarante M. Fagnoni Aryl cation chemistry as an emerging versatile tool for metal-free arylations Synlett 2008 787 800
    • (2008) Synlett , pp. 787-800
    • Dichiarante, V.1    Fagnoni, M.2
  • 13
    • 26644451618 scopus 로고    scopus 로고
    • N1 path via phenyl cation as an alternative to metal catalysis
    • N1 path via phenyl cation as an alternative to metal catalysis Acc. Chem. Res. 2005 38 713 721
    • (2005) Acc. Chem. Res. , vol.38 , pp. 713-721
    • Fagnoni, M.1    Albini, A.2
  • 15
    • 15444374961 scopus 로고    scopus 로고
    • Metal-free cross-coupling reactions of aryl sulfonates and phosphates through photoeterolysis of aryl-oxygen bonds
    • M. De Carolis S. Protti M. Fagnoni A. Albini Metal-free cross-coupling reactions of aryl sulfonates and phosphates through photoeterolysis of aryl-oxygen bonds Angew. Chem., Int. Ed. 2005 44 1232 1236
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1232-1236
    • De Carolis, M.1    Protti, S.2    Fagnoni, M.3    Albini, A.4
  • 18
    • 0034584060 scopus 로고    scopus 로고
    • Synthesis and evaluation of novel acid amplifiers liberating fluoroalkanesulfonic acids
    • S. Lee K. Arimitsu S.-W. Park K. Ichimura Synthesis and evaluation of novel acid amplifiers liberating fluoroalkanesulfonic acids J. Photopolym. Sci. Technol. 2000 13 215 216
    • (2000) J. Photopolym. Sci. Technol. , vol.13 , pp. 215-216
    • Lee, S.1    Arimitsu, K.2    Park, S.-W.3    Ichimura, K.4
  • 20
    • 48249120373 scopus 로고    scopus 로고
    • Phosphate esters as "tunable" reagents in organic synthesis
    • S. Protti M. Fagnoni Phosphate esters as "tunable" reagents in organic synthesis Chem. Commun. 2008 3611 3621
    • (2008) Chem. Commun. , pp. 3611-3621
    • Protti, S.1    Fagnoni, M.2
  • 22
    • 33947294347 scopus 로고
    • Facile synthesis of methanesulfonate esters
    • R. K. Crossland K. L. Servis Facile synthesis of methanesulfonate esters J. Org. Chem. 1970 35 3195 3196
    • (1970) J. Org. Chem. , vol.35 , pp. 3195-3196
    • Crossland, R.K.1    Servis, K.L.2
  • 23
    • 40949154756 scopus 로고    scopus 로고
    • Palladium-catalyzed carbonylation of aryl tosylates and mesylates
    • R. H. Munday J. R. Martinelli S. L. Buchwald Palladium-catalyzed carbonylation of aryl tosylates and mesylates J. Am. Chem. Soc. 2008 130 2754 2755
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 2754-2755
    • Munday, R.H.1    Martinelli, J.R.2    Buchwald, S.L.3
  • 25
    • 0344064354 scopus 로고    scopus 로고
    • Palladium-catalyzed phosphination of functionalized aryl triflates
    • F. Y. Kwong C. W. Lai M. Yu Y. Tian K. S. Chan Palladium-catalyzed phosphination of functionalized aryl triflates Tetrahedron 2003 59 10295 10305
    • (2003) Tetrahedron , vol.59 , pp. 10295-10305
    • Kwong, F.Y.1    Lai, C.W.2    Yu, M.3    Tian, Y.4    Chan, K.S.5
  • 26
    • 1242307375 scopus 로고    scopus 로고
    • Preparation and palladium-catalyzed cross-coupling of aryl triethylammonium bis(catechol) silicates with aryl triflates
    • W. M. Seganish P. DeShong Preparation and palladium-catalyzed cross-coupling of aryl triethylammonium bis(catechol) silicates with aryl triflates J. Org. Chem. 2004 69 1137 1143
    • (2004) J. Org. Chem. , vol.69 , pp. 1137-1143
    • Seganish, W.M.1    Deshong, P.2
  • 27
  • 28
    • 84981464095 scopus 로고
    • Sila-Pharmaka, 22. Cholinesterase-hemmende organophosphorsäureester und ihre sila-analoga
    • R. Tacke M. Strecker R. Niedner Sila-Pharmaka, 22. Cholinesterase- hemmende organophosphorsäureester und ihre sila-analoga Liebigs Ann. Chem. 1981 1981 387 395
    • (1981) Liebigs Ann. Chem. , vol.1981 , pp. 387-395
    • Tacke, R.1    Strecker, M.2    Niedner, R.3
  • 31
    • 67650447070 scopus 로고    scopus 로고
    • Eco-friendly hydrodehalogenation of electron-rich aryl chlorides and fluorides by photochemical reaction
    • V. Dichiarante M. Fagnoni A. Albini Eco-friendly hydrodehalogenation of electron-rich aryl chlorides and fluorides by photochemical reaction Green Chem. 2009 11 942 945
    • (2009) Green Chem. , vol.11 , pp. 942-945
    • Dichiarante, V.1    Fagnoni, M.2    Albini, A.3
  • 33
    • 78650748833 scopus 로고    scopus 로고
    • note
    • Studies on the photodecomposition of phenyldiazonium ions demonstrated that singet phenyl cations add non-selectively even to weak nucleophiles. See:
  • 34
    • 0037239338 scopus 로고    scopus 로고
    • Cationic arylation through photo(sensitised) decomposition of diazonium salts. Chemoselectivity of triplet phenyl cations
    • See, for example:
    • S. Milanesi M. Fagnoni A. Albini Cationic arylation through photo(sensitised) decomposition of diazonium salts. Chemoselectivity of triplet phenyl cations Chem. Commun. 2003 216 217
    • (2003) Chem. Commun. , pp. 216-217
    • Milanesi, S.1    Fagnoni, M.2    Albini, A.3
  • 36
    • 0031562123 scopus 로고    scopus 로고
    • Unsensitized photooxidation of sulfur compounds with molecular oxygen in solution
    • E. Robert-Banchereau S. Lacombe J. Ollivier Unsensitized photooxidation of sulfur compounds with molecular oxygen in solution Tetrahedron 1997 53 2087 2102
    • (1997) Tetrahedron , vol.53 , pp. 2087-2102
    • Robert-Banchereau, E.1    Lacombe, S.2    Ollivier, J.3
  • 38
    • 0345378575 scopus 로고
    • Sulfochloration of trifluoromethane. Theoretical study of the trifluoromethane sulfonyl radical
    • D. Gonbeau M. F. Guimon S. Duplantier J. Ollivier G. Pfister-Guillouzo Sulfochloration of trifluoromethane. Theoretical study of the trifluoromethane sulfonyl radical Chem. Phys. 1989 135 85 89
    • (1989) Chem. Phys. , vol.135 , pp. 85-89
    • Gonbeau, D.1    Guimon, M.F.2    Duplantier, S.3    Ollivier, J.4    Pfister-Guillouzo, G.5
  • 39
    • 33947441975 scopus 로고
    • The behavior of sulfur dioxide as an acid in methanol
    • L. S. Guss I. M. Kolthoff The behavior of sulfur dioxide as an acid in methanol J. Am. Chem. Soc. 1944 66 1484 1488
    • (1944) J. Am. Chem. Soc. , vol.66 , pp. 1484-1488
    • Guss, L.S.1    Kolthoff, I.M.2
  • 40
    • 0041551983 scopus 로고
    • Nebenreaktionen in Karl-Fischer-reagentien
    • A. Seubert G. Wünsch Nebenreaktionen in Karl-Fischer-reagentien Fresenius' Z. Anal. Chem. 1989 334 256 260
    • (1989) Fresenius' Z. Anal. Chem. , vol.334 , pp. 256-260
    • Seubert, A.1    Wünsch, G.2
  • 41
    • 37049126898 scopus 로고
    • Reactions of radicals containing fluorine. Part 1. Hydrogen and deuterium atom abstraction from trideuteromethanol by trifluoromethyl radicals
    • E. R. Morris J. C. J. Thynne Reactions of radicals containing fluorine. Part 1. Hydrogen and deuterium atom abstraction from trideuteromethanol by trifluoromethyl radicals Trans. Faraday Soc. 1968 64 414 421
    • (1968) Trans. Faraday Soc. , vol.64 , pp. 414-421
    • Morris, E.R.1    Thynne, J.C.J.2
  • 42
    • 0038984395 scopus 로고
    • Lifetime of trifluoromethyl radical in aqueous solution
    • J. Lillie D. Behar R. J. Sujdak R. H. Schuler Lifetime of trifluoromethyl radical in aqueous solution J. Phys. Chem. 1972 76 2517 2520
    • (1972) J. Phys. Chem. , vol.76 , pp. 2517-2520
    • Lillie, J.1    Behar, D.2    Sujdak, R.J.3    Schuler, R.H.4
  • 44
    • 23244433646 scopus 로고    scopus 로고
    • Synthesis of α,ω-dimethoxyfluoropolyethers: Reaction mechanism and kinetics
    • M. Avataneo U. De Patto M. Galimberti G. Marchionni Synthesis of α,ω-dimethoxyfluoropolyethers: reaction mechanism and kinetics J. Fluorine Chem. 2005 126 631 637
    • (2005) J. Fluorine Chem. , vol.126 , pp. 631-637
    • Avataneo, M.1    De Patto, U.2    Galimberti, M.3    Marchionni, G.4
  • 45
    • 0035528875 scopus 로고    scopus 로고
    • OH-Radical-induced oxidation of methanesulfinic acid. the reactions of the methanesulfonyl radical in the absence and presence of dioxygen
    • R. Flyunt O. Makogon M. N. Schuchmann K.-D. Asmus C. von Sonntag OH-Radical-induced oxidation of methanesulfinic acid. The reactions of the methanesulfonyl radical in the absence and presence of dioxygen J. Chem. Soc., Perkin Trans. 2 2001 787 792
    • (2001) J. Chem. Soc., Perkin Trans. 2 , pp. 787-792
    • Flyunt, R.1    Makogon, O.2    Schuchmann, M.N.3    Asmus, K.-D.4    Von Sonntag, C.5


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