메뉴 건너뛰기




Volumn 10, Issue 9, 2011, Pages 1450-1454

Photochemistry of 2-diphenylmethoxyacetophenone. Direct detection of a long-lived enol from a Norrish Type II photoreaction

Author keywords

[No Author keywords available]

Indexed keywords


EID: 80052216117     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c1pp05095h     Document Type: Article
Times cited : (5)

References (29)
  • 2
    • 0001658207 scopus 로고
    • O-Nitrophenylethylene Glycol: A Photosensitive Protecting Group for Aldehydes and Ketones
    • J. Hébert D. Gravel o-Nitrophenylethylene Glycol: a Photosensitive Protecting Group for Aldehydes and Ketones Can. J. Chem. 1974 52 187 189
    • (1974) Can. J. Chem. , vol.52 , pp. 187-189
    • Hébert, J.1    Gravel, D.2
  • 3
    • 37049092655 scopus 로고
    • O-Nitrobenzyl alcohol, a simple and efficient reagent for the photoreversible protection of aldehydes and ketones
    • D. Gravel S. Murray G. Ladouceur o-Nitrobenzyl alcohol, a simple and efficient reagent for the photoreversible protection of aldehydes and ketones J. Chem. Soc., Chem. Commun. 1985 1828 1829
    • (1985) J. Chem. Soc., Chem. Commun. , pp. 1828-1829
    • Gravel, D.1    Murray, S.2    Ladouceur, G.3
  • 4
    • 0037423175 scopus 로고    scopus 로고
    • Bis(o-nitrophenyl)ethanediol: A practical photolabile protecting group for ketones and aldehydes
    • DOI 10.1021/jo026347x
    • A. Blanc C. G. Bochet Bis(o-nitrophenyl)ethanediol: A Practical Photolabile Protecting Group for Ketones and Aldehydes J. Org. Chem. 2003 68 1138 1141 (Pubitemid 36176644)
    • (2003) Journal of Organic Chemistry , vol.68 , Issue.3 , pp. 1138-1141
    • Blanc, A.1    Bochet, C.G.2
  • 5
    • 34247510198 scopus 로고    scopus 로고
    • Novel Photolabile Protecting Group for Carbonyl Compounds
    • Although utility of the phenacyl ester based protecting groups are well known, this protecting group is not used for the protection of ketones
    • P. Wang H. Hu Y. Wang Novel Photolabile Protecting Group for Carbonyl Compounds Org. Lett. 2007 9 1533 1535
    • (2007) Org. Lett. , vol.9 , pp. 1533-1535
    • Wang, P.1    Hu, H.2    Wang, Y.3
  • 6
    • 0030755239 scopus 로고    scopus 로고
    • New photoactivated protecting groups. 7. p-Hydroxyphenacyl: A phototrigger for excitatory amino acids and peptides
    • DOI 10.1021/ja971331n
    • R. S. Givens A. Jung C.-H. Park J. Weber W. Bartlett New Photoactivated Protecting Groups. 7. p-Hydroxyphenacyl: A Phototrigger for Excitatory Amino Acids and Peptides J. Am. Chem. Soc. 1997 119 8369 8370 (Pubitemid 27390640)
    • (1997) Journal of the American Chemical Society , vol.119 , Issue.35 , pp. 8369-8370
    • Givens, R.S.1    Jung, A.2    Park, C.-H.3    Weber, J.4    Bartlett, W.5
  • 7
    • 0000897083 scopus 로고
    • Photochemistry of phosphate esters: α-keto phosphates as a photoprotecting group for caged phosphate
    • R. S. Givens P. S. Athey B. Matuszewski L. W. KueperIII J. Xue T. Fister Photochemistry of phosphate esters: α-keto phosphates as a photoprotecting group for caged phosphate J. Am. Chem. Soc. 1993 115 6001 6012
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 6001-6012
    • Givens, R.S.1    Athey, P.S.2    Matuszewski, B.3    Kueper Iii, L.W.4    Xue, J.5    Fister, T.6
  • 10
    • 77954179897 scopus 로고    scopus 로고
    • Kinetic studies of keto-enol and other tautomeric equilibria by flash photolysis
    • J. Wirz Kinetic studies of keto-enol and other tautomeric equilibria by flash photolysis Adv. Phys. Org. Chem. 2010 44 325 356
    • (2010) Adv. Phys. Org. Chem. , vol.44 , pp. 325-356
    • Wirz, J.1
  • 11
    • 0010449212 scopus 로고    scopus 로고
    • Photochemical reactions involving enols
    • ed. Z. Rappoport, John Wiley & Sons Inc
    • A. C. Weedon, Photochemical reactions involving enols, in Enols (1990), ed., Z. Rappoport, John Wiley & Sons Inc, 2010, pp. 591-638
    • (2010) Enols (1990) , pp. 591-638
    • Weedon, A.C.1
  • 12
    • 0002905711 scopus 로고
    • Flash Photolytic Generation and Study of Reactive Species: From Enol to Ynols
    • A. J. Kresge Flash Photolytic Generation and Study of Reactive Species: From Enol to Ynols Acc. Chem. Res. 1990 23 43 48
    • (1990) Acc. Chem. Res. , vol.23 , pp. 43-48
    • Kresge, A.J.1
  • 13
    • 33947482015 scopus 로고
    • Detection and Lifetime of Enol-Acetone in the Photolysis of 2-Pentanone Vapor
    • G. R. McMillan J. G. Calvert J. N. Pitts Detection and Lifetime of Enol-Acetone in the Photolysis of 2-Pentanone Vapor J. Am. Chem. Soc. 1964 86 3602 3605
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 3602-3605
    • McMillan, G.R.1    Calvert, J.G.2    Pitts, J.N.3
  • 14
    • 37049142326 scopus 로고
    • The detection of ethylketen and enol-crotonaldehyde in the vapour-phase photolysis of trans-crotonaldehyde
    • J. W. Coomber J. N. Pitts R. R. Schrock The detection of ethylketen and enol-crotonaldehyde in the vapour-phase photolysis of trans-crotonaldehyde Chem. Commun. 1968 190b 191
    • (1968) Chem. Commun.
    • Coomber, J.W.1    Pitts, J.N.2    Schrock, R.R.3
  • 15
    • 84980140075 scopus 로고
    • Enols from Norrish Type II Cleavage of Carbonyl Compounds in Solution
    • A. Henne H. Fischer Enols from Norrish Type II Cleavage of Carbonyl Compounds in Solution Angew. Chem., Int. Ed. Engl. 1976 15 435 435
    • (1976) Angew. Chem., Int. Ed. Engl. , vol.15 , pp. 435-435
    • Henne, A.1    Fischer, H.2
  • 16
    • 0013659490 scopus 로고
    • Photo-CIDNP [chemically induced dynamic nuclear polarization] detection of transient intermediates. Enol of acetophenone
    • S. M. Rosenfeld R. G. Lawler H. R. Ward Photo-CIDNP [chemically induced dynamic nuclear polarization] detection of transient intermediates. Enol of acetophenone J. Am. Chem. Soc. 1973 95 946 948
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 946-948
    • Rosenfeld, S.M.1    Lawler, R.G.2    Ward, H.R.3
  • 17
    • 84858287424 scopus 로고
    • Type II reactions from the photolysis of the phenacyl ether of 1,2:3,4-di-O-isopropylidene-α-D-Galactopyranose
    • R. W. Binkley H. F. Jarrell Type II reactions from the photolysis of the phenacyl ether of 1,2:3,4-di-O-isopropylidene-α-D-Galactopyranose J. Carbohydr., Nucleosides, Nucleotides 1980 7 347 364
    • (1980) J. Carbohydr., Nucleosides, Nucleotides , vol.7 , pp. 347-364
    • Binkley, R.W.1    Jarrell, H.F.2
  • 18
    • 0000801694 scopus 로고
    • Effects of Intermolecular Hydrogen-bonding on the Luminescence Properties of Acetophenone, Characterization of Emission States
    • S. K. Ghoshal S. K. Sarkar G. S. Kastha Effects of Intermolecular Hydrogen-bonding on the Luminescence Properties of Acetophenone, Characterization of Emission States Bull. Chem. Soc. Jpn. 1981 54 3556 3561
    • (1981) Bull. Chem. Soc. Jpn. , vol.54 , pp. 3556-3561
    • Ghoshal, S.K.1    Sarkar, S.K.2    Kastha, G.S.3
  • 20
    • 0037123204 scopus 로고    scopus 로고
    • A comparative photomechanistic study (spin trapping, EPR spectroscopy, transient kinetics, photoproducts) of nucleoside oxidation (dG and 8-oxodG) by triplet-excited acetophenones and by the radicals generated from α-oxy-substituted derivatives through norrish-type I cleavage
    • DOI 10.1021/ja017600y
    • W. Adam M. A. Arnold W. M. Nau U. Pischel C. R. Saha-Mller A Comparative Photomechanistic Study (Spin Trapping, EPR Spectroscopy, Transient Kinetics, Photoproducts) of Nucleoside Oxidation (dG and 8-oxodG) by Triplet-Excited Acetophenones and by the Radicals Generated from α-Oxy-Substituted Derivatives through Norrish-Type I Cleavage J. Am. Chem. Soc. 2002 124 3893 3904 (Pubitemid 34310904)
    • (2002) Journal of the American Chemical Society , vol.124 , Issue.15 , pp. 3893-3904
    • Adam, W.1    Arnold, M.A.2    Nau, W.M.3    Pischel, U.4    Saha-Moller, C.R.5
  • 21
    • 49949129254 scopus 로고
    • Type II photoelimination and 3-oxetanol formation from α-alkoxyacetophenones
    • N. J. Turro F. D. Lewis Type II photoelimination and 3-oxetanol formation from α-alkoxyacetophenones Tetrahedron Lett. 1968 9 5845 5848
    • (1968) Tetrahedron Lett. , vol.9 , pp. 5845-5848
    • Turro, N.J.1    Lewis, F.D.2
  • 22
    • 0001249057 scopus 로고
    • Molecular Photochemistry. XVIII. Type II Photoelimination and 3-Oxetanol Formation from α-Alkoxyacetophenones and Related Compounds
    • F. Lewis N. Turro Molecular Photochemistry. XVIII. Type II Photoelimination and 3-Oxetanol Formation from α-Alkoxyacetophenones and Related Compounds J. Am. Chem. Soc. 1970 92 311 320
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 311-320
    • Lewis, F.1    Turro, N.2
  • 23
    • 0000310734 scopus 로고
    • Photochemical Generation of Radical Anions of Photolabile Aryl Ketones
    • N. Mathivanan L. J. Johnston D. D. M. Wayner Photochemical Generation of Radical Anions of Photolabile Aryl Ketones J. Phys. Chem. 1995 99 8190 8195
    • (1995) J. Phys. Chem. , vol.99 , pp. 8190-8195
    • Mathivanan, N.1    Johnston, L.J.2    Wayner, D.D.M.3
  • 24
    • 0000049828 scopus 로고
    • Evidence for singlet state β-cleavage in the photoreaction of α-(2,6-dimethoxyphenoxy)-acetophenone inferred from time-resolved CIDNP spectroscopy
    • W. U. Palm H. Dreeskamp Evidence for singlet state β-cleavage in the photoreaction of α-(2,6-dimethoxyphenoxy)-acetophenone inferred from time-resolved CIDNP spectroscopy J. Photochem. Photobiol., A 1990 52 439 450
    • (1990) J. Photochem. Photobiol., A , vol.52 , pp. 439-450
    • Palm, W.U.1    Dreeskamp, H.2
  • 25
    • 0040732560 scopus 로고
    • Photochemistry of α-phenoxy-p-methoxyacetophenone
    • J. C. Netto-Ferreira J. C. Scaiano Photochemistry of α-phenoxy-p- methoxyacetophenone Tetrahedron Lett. 1989 30 443 446
    • (1989) Tetrahedron Lett. , vol.30 , pp. 443-446
    • Netto-Ferreira, J.C.1    Scaiano, J.C.2
  • 26
    • 0000033820 scopus 로고
    • Solvent effects on type II photoelimination of phenyl ketones
    • P. J. Wagner Solvent effects on type II photoelimination of phenyl ketones J. Am. Chem. Soc. 1967 89 5898 5901
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 5898-5901
    • Wagner, P.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.