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Abstract:

The photochemistry of tris(p-bromophenyl)amine was investigated in a nitrogen- and oxygen-flushed solution under laser flash photolysis conditions. The detected intermediates were the corresponding amine radical cation ("Magic Blue") and the N-phenyl-4a,4b-dihydrocarbazole radical cation that, under an oxygen atmosphere, is converted to the corresponding hydroperoxyl radical. The role of the last species was supported by the smooth co-oxidation of sulfides to sulfoxides. On the other hand, co-oxidation of nucleophilic triarylphosphines to triarylphosphine oxides arose from an electron transfer between the photogenerated "Magic Blue" and phosphine that prevented the amine cyclization. In this case, intermediate Ar3POO•+ was found to play a key role in phosphine oxide formation. © 2018 American Chemical Society.

Registro:

Documento: Artículo
Título:Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study
Autor:Bonesi, S.M.; Protti, S.; Albini, A.
Filiación:Departamento de Química Orgánica, CIHIDECAR-CONICET, 3er Piso, Ciudad Universitaria, FCEyN, University of Buenos Aires, Pabellón 2, Buenos Aires, 1428, Argentina
PhotoGreen Lab, Department of Chemistry, University of Pavia, V. leTaramelli 12, Pavia, 27100, Italy
Palabras clave:Electron transport properties; Free radical reactions; Oxidation; Oxygen; Photolysis; Positive ions; Sulfur compounds; Electron transfer process; Hydroperoxyl radical; Laser flash photolysis; Mechanistic studies; Oxygen atmosphere; Phosphine oxide; Radical cations; Triarylphosphines; Phosphorus compounds; amine; aniline derivative; bromine derivative; carbazole derivative; cation; nitrogen; oxygen; phosphine derivative; radical; sulfide; sulfoxide; Article; cyclization; electron transport; flash photolysis; nucleophilicity; oxidation; photochemistry
Año:2018
Volumen:83
Número:15
Página de inicio:8104
Página de fin:8113
DOI: http://dx.doi.org/10.1021/acs.joc.8b00913
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:nitrogen, 7727-37-9; oxygen, 7782-44-7; sulfide, 18496-25-8; sulfoxide, 120-62-7
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v83_n15_p8104_Bonesi

Referencias:

  • Plesniak, M.P., Huang, H.-M., Procter, D.J., Radical cascade reactions triggered by single electron transfer (2017) Nature Rev. Chem., 1, p. 0077
  • Lligadas, G., Grama, S., Percec, V., Single-Electron Transfer Living Radical Polymerization Platform to Practice, Develop, and Invent (2017) Biomacromolecules, 18, pp. 2981-3008
  • Zhang, N., Samanta, S.R., Rosen, B.M., Percec, V., Single Electron Transfer in Radical Ion and Radical-Mediated Organic, Materials and Polymer Synthesis (2014) Chem. Rev., 114, pp. 5848-5958
  • Branchini, B.R., Behney, C.E., Southworth, T.L., Fontaine, D.M., Gulick, A.M., Vinyard, D.J., Brudvig, G.W., Experimental Support for a Single Electron-Transfer Oxidation Mechanism in Firefly Bioluminescence (2015) J. Am. Chem. Soc., 137, pp. 7592-7595
  • Creutz, S.E., Lotito, K.J., Fu, G.C., Peters, J.C., Photoinduced Ullmann C-N Coupling: Demonstrating the Viability of a Radical Pathway (2012) Science, 338 (6107), pp. 647-651
  • Quiroz-Guzman, M., Brown, S.N., Tris(4-bromo-phenyl)aminium hexachloroantimonate (Magic Blue'): A strong oxidant with low inner-sphere reorganization (2010) Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 66, pp. m171-m173
  • Breslin, D.T., Fox, M.A., Photochemical Electrocyclization of Thermally Stable Triarylamine Radical Cations (1994) J. Org. Chem., 59, pp. 7557-7561
  • Breslin, D.T., Fox, M.A., Excited-State Behavior of Thermally Stable Radical Ions (1994) J. Phys. Chem., 98, pp. 408-411
  • Yurchenko, O., Freytag, D., Zur Borg, L., Zentel, R., Heinze, J., Ludwigs, S., Electrochemically Induced Reversible and Irreversible Coupling of Triarylamines (2012) J. Phys. Chem. B, 116, pp. 30-39
  • Baranoff, E., Dixon, I.M., Collin, J.P., Sauvage, J.P., Ventura, B., Flamigni, L., Dyads Containing Iridium(III) Bis-terpyridine as Photoactive Center: Synthesis and Electron Transfer Study (2004) Inorg. Chem., 43, pp. 3057-3066
  • Flamigni, L., Baranoff, E., Collin, J.P., Sauvage, J.P., A Triad Based on an Iridium(III) Bisterpyridine Complex Leading to a Charge-Separated State with a 120-μs Lifetime at Room Temperature (2006) Chem. - Eur. J., 12, pp. 6592-6606
  • Bonesi, S.M., Dondi, D., Protti, S., Fagnoni, M., Albini, A., (Co)oxidation/cyclization processes upon irradiation of triphenylamine (2014) Tetrahedron Lett., 55, pp. 2932-2935
  • Wilkinson, F., Abdel-Shafi, A.A., Mechanism of Quenching of Triplet States by Oxygen: Biphenyl Derivatives in Acetonitrile (1997) J. Phys. Chem. A, 101, pp. 5509-5516
  • Silva, E.F.F., Serpa, C., Dabrowski, J.M., Monteiro, C.J.P., Formosinho, S.J., Stochel, G., Urbanska, K., Arnaut, L.G., Mechanisms of Singlet-Oxygen and Superoxide-Ion Generation by Porphyrins and Bacteriochlorins and their Implications in Photodynamic Therapy (2010) Chem. - Eur. J., 16, pp. 9273-9286
  • Abdel-Shafi, A.A., Wilkinson, F., Electronic to vibrational energy conversion and charge transfer contributions during quenching by molecular oxygen of electronically excited triplet states (2002) Phys. Chem. Chem. Phys., 4, pp. 248-254
  • Abdel-Shafi, A.A., Wilkinson, F., Charge Transfer Effects on the Efficiency of Singlet Oxygen Production Following Oxygen Quenching of Excited Singlet and Triplet States of Aromatic Hydrocarbons in Acetonitrile (2000) J. Phys. Chem. A, 104, pp. 5747-5757
  • Liang, J.J., Gu, C.L., Kacher, M.L., Foote, C.S., Chemistry of singlet oxygen. 45. Mechanism of the photooxidation of sulfides (1983) J. Am. Chem. Soc., 105, pp. 4717-4721
  • Parisien-Collette, S., Hernández-Pérez, A.C., Collins, Sh.K., Photochemical Synthesis of Carbazoles Using an [Fe(phen)3](NTf2)2/O2 Catalyst System: Catalysis toward Sustainability (2016) Org. Lett., 18, pp. 4994-4997
  • Amthor, S., Noller, B., Lambert, C., UV/Vis/NIR spectral properties of triarylamines and their corresponding radical cations (2005) Chem. Phys., 316, pp. 141-152
  • Ambrose, J.F., Carpenter, L.L., Nelson, R.F., Electrochemical and Spectroscopic Properties of Cation Radicals III. Reaction Pathways of Carbazolium Radical Ions (1975) J. Electrochem. Soc., 122, pp. 876-894
  • Cho, S.H., Yoon, J., Chang, S., Intramolecular Oxidative C-N Bond Formation for the Synthesis of Carbazoles: Comparison of Reactivity between the Copper-Catalyzed and Metal-Free Conditions (2011) J. Am. Chem. Soc., 133, pp. 5996-6005
  • Jordan-Hore, J.A., Johansson, C.C.C., Gulias, M., Beck, E.M., Gaunt, M.J., Oxidative Pd(II)-Catalyzed C-H Bond Amination to Carbazole at Ambient Temperature (2008) J. Am. Chem. Soc., 130, pp. 16184-16186
  • Sridharan, V., Martin, M.A., Menéndez, J.C., Synthesis of Oxygenated Carbazoles by Palladium-Mediated Oxidative Double C-H Activation of Diarylamines Assisted by Microwave Irradiation (2006) Synlett, 2006, pp. 2375-2378
  • Hernández-Pérez, A.C., Collins, S.K., A visible-light-mediated synthesis of carbazoles (2013) Angew. Chem., Int. Ed., 52, pp. 12696-12700
  • Hernández-Pérez, A.C., Caron, A., Collins, S.K., Photochemical Synthesis of Complex Carbazoles: Evaluation of Electronic Effects in Both UV- and Visible-Light Methods in Continuous Flow (2015) Chem. - Eur. J., 21, pp. 16673-16678
  • Bedford, R.B., Betham, M., N-H Carbazole Synthesis from 2-Chloroanilines via Consecutive Amination and C-H Activation (2006) J. Org. Chem., 71, pp. 9403-9410
  • Bedford, R.B., Cazin, C.S.J., A novel catalytic one-pot synthesis of carbazoles via consecutive amination and C-H activation (2002) Chem. Commun., pp. 2310-3211
  • Buxton, G.V., Greenstock, C.L., Helman, W.P., Ross, A.B., Critical Review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (·OH/·O- in Aqueous Solution (1988) J. Phys. Chem. Ref. Data, 17, p. 513
  • Janata, E., Direct optical observation of the formation of some aliphatic alcohol radicals. A pulse radiolysis study (2002) Proc. - Indian Acad. Sci., Chem. Sci., 114, pp. 731-737
  • Hare, P.M., Price, E.A., Stanisky, Ch.M., Janik, I., Bartels, D.M., Solvated Electron Extinction Coefficient and Oscillator Strength in High Temperature Water (2010) J. Phys. Chem. A, 114, pp. 1766-1775
  • Lemmon, R.M., Pohlit, H.M., Erwin, W., Lin, T.-H., Hot-atom chemistry of carbon-14 in solid benzene at kinetic energies between 5 and 100 eV (1971) J. Phys. Chem., 75, pp. 2555-2557
  • Wolfenden, B.S., Willson, R.L., Radical-cations as reference chromogens in kinetic studies of ono-electron transfer reactions: Pulse radiolysis studies of 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulphonate) (1982) J. Chem. Soc., Perkin Trans. 2, pp. 805-812
  • Wala, M., Bothe, E., Goerner, H., Schulte-Frohlinde, D., Quantum yields for the generation of hydrated electrons and single-strand breaks in poly(C), poly(A) and single-stranded DNA in aqueous solution on 20 ns laser excitation at 248 nm (1990) J. Photochem. Photobiol., A, 53, pp. 87-108
  • Bonesi, S.M., Mella, M., D'Alessandro, N., Aloisi, A., Vanossi, M., Albini, A., Photosensitized oxygenation of benzyl ethyl sulfide (1998) J. Org. Chem., 63, pp. 9946-9955
  • Bonesi, S.M., Torriani, R., Mella, M., Albini, A., The photooxygenation of benzyl, heteroarylmethyl and allyl sulfides (1999) Eur. J. Org. Chem., 1999, pp. 1723-1728
  • Bonesi, S.M., Fagnoni, M., Albini, A., Hammett correlations in the photosensitized oxidation of 4-substituted thioanisoles (2004) J. Org. Chem., 69, pp. 928-935
  • Clennan, E.L., Persulfoxide: Key Intermediate in Reactions of Singlet Oxygen with Sulfides (2001) Acc. Chem. Res., 34, pp. 875-884
  • Hermans, I., Peeters, J., Jacobs, P.A., Autoxidation of Hydrocarbons: From Chemistry to Catalysis (2008) Top. Catal., 50, pp. 124-132
  • Reynolds, R., Line, L.L., Nelson, R.F., Electrochemical generation of carbazoles from aromatic amines (1974) J. Am. Chem. Soc., 96, pp. 1087-1092
  • Goto, Y., Matsui, T., Ozaki, S., Watanabe, Y., Fukuzumi, S., Mechanisms of Sulfoxidation Catalyzed by High-Valent Intermediates of Heme Enzymes: Electron-Transfer vs Oxygen-Transfer Mechanism (1999) J. Am. Chem. Soc., 121, pp. 9497-9502
  • Baciocchi, E., Del Giacco, T., Elisei, F., Gerini, M.F., Guerra, M., Lapi, A., Liberali, P., Electron Transfer and Singlet Oxygen Mechanisms in the Photooxygenation of Dibutyl Sulfide and Thioanisole in MeCN Sensitized by N-Methylquinolinium Tetrafluoborate and 9,10-Dicyanoanthracene. the Probable Involvement of a Thiadioxirane Intermediate in Electron Transfer Photooxygenations (2003) J. Am. Chem. Soc., 125, pp. 16444-16454
  • Bonesi, S.M., Manet, I., Freccero, M., Fagnoni, M., Albini, A., Photosensitized oxidation of Sulfides: Discriminating between the Singlet-Oxygen Mechanism and Electron Transfer Involving Superoxide Anion or Molecular Oxygen (2006) Chem. - Eur. J., 12, pp. 4844-4857
  • Nakamura, M., Miki, M., Majima, T., Substituent effect on the photoinduced electron-transfer reaction of para-substituted triphenyl phosphines sensitised by 9,10-dicyanoanthracene (2000) J. Chem. Soc., Perkin Trans., 2, pp. 1447-1452
  • Lalevée, J., Allonas, X., Fouassier, J.P., New access to the peroxyl radicals reactivity? (2007) Chem. Phys. Lett., 445, pp. 62-67
  • Fukuzumi, S., Shimoosako, K., Suenobu, T., Watanabe, Y., Mechanisms of Hydrogen-, Oxygen-, and Electron-Transfer Reactions of Cumylperoxyl Radical (2003) J. Am. Chem. Soc., 125, pp. 9074-9082
  • Yasui, S., Rahman Badal, M., Kobayashi, S., Mishima, M., Combination of LFP-TRIR spectroscopy and DFT computation as a tool to determine the intermediate during the photooxidation of triarylphosphine (2014) J. Phys. Org. Chem., 27, pp. 967-972
  • Yasui, S., Rahman Badal, M., Kobayashi, S., Mishima, M., Kinetic study of photoreaction of triarylphosphines by laser flash photolysis time-resolved UV-VIS spectroscopy (2013) Chem. Lett., 42, pp. 866-868
  • Ohkubo, K., Nanjo, T., Fukuzumi, S., Photocatalytic Electron-Transfer Oxidation of Triphenylphosphine and Benzylamine with Molecular Oxygen via Formation of Radical Cations and Superoxide Ion (2006) Bull. Chem. Soc. Jpn., 79, pp. 1489-1500
  • Beaver, B., Rawlings, D., Neta, P., Alfassi, Z.B., Das, T.N., Structural effects on the reactivity of substituted arylphosphines as potential oxygen-scavenging additives for future jet fuels (1998) Heteroat. Chem., 9, pp. 133-138
  • Bonesi, S.M., Protti, S., Albini, A., Reactive Oxygen Species (ROS)-vs Peroxyl-Mediated Photosensitized Oxidation of Triphenylphosphine: A Comparative Study (2016) J. Org. Chem., 81, pp. 11678-11685
  • Zhang, D., Ye, B., Ho, D.G., Gao, R., Selke, M., Chemistry of singlet oxygen with arylphosphines (2006) Tetrahedron, 62, pp. 10729-10733
  • Bordwell, F.G., Boutan, P., Synthesis of Aryl Methyl Sulfoxides and Determination of the Conjugative Effect of the Methylsulfinyl Group (1957) J. Am. Chem. Soc., 79, pp. 717-722
  • Senear, A.E., Valient, W., Wirth, J., Derivatives of Triphenylphosphine and Triphenylphosphine Oxide (1960) J. Org. Chem., 25, pp. 2001-2006
  • Modena, G., Taddei, F., Todesco, P.E., Nucleophilic substitutions in ethylene derivatives: 1-arylsulfonyl-1-methyl-2-haloethylenes (1960) Gazz. Chim. Ital., 89, p. 894
  • Cerniani, A., Modena, G., Todesco, P.E., Oxidation of organic sulfides. IV. Oxidation of benzyl and phenyl alkyl sulfoxides to sulfones (1960) Gazz. Chim. Ital., 90, p. 3

Citas:

---------- APA ----------
Bonesi, S.M., Protti, S. & Albini, A. (2018) . Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study. Journal of Organic Chemistry, 83(15), 8104-8113.
http://dx.doi.org/10.1021/acs.joc.8b00913
---------- CHICAGO ----------
Bonesi, S.M., Protti, S., Albini, A. "Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study" . Journal of Organic Chemistry 83, no. 15 (2018) : 8104-8113.
http://dx.doi.org/10.1021/acs.joc.8b00913
---------- MLA ----------
Bonesi, S.M., Protti, S., Albini, A. "Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study" . Journal of Organic Chemistry, vol. 83, no. 15, 2018, pp. 8104-8113.
http://dx.doi.org/10.1021/acs.joc.8b00913
---------- VANCOUVER ----------
Bonesi, S.M., Protti, S., Albini, A. Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study. J. Org. Chem. 2018;83(15):8104-8113.
http://dx.doi.org/10.1021/acs.joc.8b00913