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Mechanism of intermolecular aromatic substitution by arylnitrenes

Cite this: J. Am. Chem. Soc. 1972, 94, 4, 1374–1376
Publication Date (Print):February 1, 1972
https://doi.org/10.1021/ja00759a066
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  1. Divneet Kaur, Hoi L. Luk, William Coldren, Pavan M. Srinivas, Lakshetti Sridhar, Sripadi Prabhakar, Partha Raghunathan, T. N. Guru Row, Christopher M. Hadad, Matthew S. Platz, and Sambasivan V. Eswaran . Concomitant Nitrene and Carbene Insertion Accompanying Ring Expansion: Spectroscopic, X-ray, and Computational Studies. The Journal of Organic Chemistry 2014, 79 (3) , 1199-1205. https://doi.org/10.1021/jo402621w
  2. Jaehyeung Park and Mingdi Yan . Covalent Functionalization of Graphene with Reactive Intermediates. Accounts of Chemical Research 2013, 46 (1) , 181-189. https://doi.org/10.1021/ar300172h
  3. Matthias Filthaus, Larissa Schwertmann, Patrik Neuhaus, Rüdiger W. Seidel, Iris M. Oppel, and Holger F. Bettinger . C–H Bond Amination by Photochemically Generated Transient Borylnitrenes at Room Temperature: A Combined Experimental and Theoretical Investigation of the Insertion Mechanism and Influence of Substituents. Organometallics 2012, 31 (10) , 3894-3903. https://doi.org/10.1021/om300063y
  4. Meihua Shen and Tom G. Driver. Iron(II) Bromide-Catalyzed Synthesis of Benzimidazoles from Aryl Azides. Organic Letters 2008, 10 (15) , 3367-3370. https://doi.org/10.1021/ol801227f
  5. N. P. Gritsan and, M. S. Platz. Kinetics, Spectroscopy, and Computational Chemistry of Arylnitrenes. Chemical Reviews 2006, 106 (9) , 3844-3867. https://doi.org/10.1021/cr040055+
  6. Nina P. Gritsan,, Anna Dóra Gudmundsdóttir,, Dean Tigelaar,, Zhendong Zhu,, William L. Karney,, Christopher M. Hadad, and, Matthew S. Platz. A Laser Flash Photolysis and Quantum Chemical Study of the Fluorinated Derivatives of Singlet Phenylnitrene. Journal of the American Chemical Society 2001, 123 (9) , 1951-1962. https://doi.org/10.1021/ja9944305
  7. Nina P. Gritsan,, Igor Likhotvorik,, Meng-Lin Tsao,, Nil Çelebi,, Matthew S. Platz,, William L. Karney,, Carl R. Kemnitz, and, Weston Thatcher Borden. Ring-Expansion Reaction of Cyano-Substituted Singlet Phenyl Nitrenes:  Theoretical Predictions and Kinetic Results from Laser Flash Photolysis and Chemical Trapping Experiments. Journal of the American Chemical Society 2001, 123 (7) , 1425-1433. https://doi.org/10.1021/ja002594b
  8. Elisa Leyva, Matthew S. Platz, Silvia E. Loredo-Carrillo, Johana Aguilar. Fluoro Aryl Azides: Synthesis, Reactions and Applications. Current Organic Chemistry 2020, 24 (11) , 1161-1180. https://doi.org/10.2174/1385272824999200608132505
  9. Daria Yu Dzhons, Andrei V Budruev. Synthesis of 2,1-benzisoxazole-3(1 H )-ones by base-mediated photochemical N–O bond-forming cyclization of 2-azidobenzoic acids. Beilstein Journal of Organic Chemistry 2016, 12 , 874-881. https://doi.org/10.3762/bjoc.12.86
  10. . Diradicals and Carbenes. 2014,,, 297-372. https://doi.org/10.1002/9781118671191.ch5
  11. Elisa Leyva, Denisse de Loera, Socorro Leyva, Rogelio Jimenez-Cataño. Fluorinated Aryl Nitrene Precursors. 2013,,, 451-479. https://doi.org/10.1002/9781118560907.ch11
  12. George R. Proctor. Azepine Ring Systems Containing two Rings. 2008,,, 637-768. https://doi.org/10.1002/9780470187210.ch2
  13. . Dihydroazepinones. 2008,,, 449-480. https://doi.org/10.1002/9780470187968.ch9
  14. N P Gritsan. Study of photochemical transformations of organic azides by matrix isolation techniques and quantum chemistry. Russian Chemical Reviews 2007, 76 (12) , 1139-1160. https://doi.org/10.1070/RC2007v076n12ABEH003702
  15. Gary B. Schuster, Matthew S. Platz. Photochemistry of Phenyl Azide. 2007,,, 69-143. https://doi.org/10.1002/9780470133484.ch2
  16. Yehia A Ibrahim, Nouria A Al-Awadi, Kamini Kual. Flash vacuum pyrolysis of azo and nitrosophenols: new routes towards hydroxyarylnitrenes and their reactions. Tetrahedron 2003, 59 (29) , 5425-5430. https://doi.org/10.1016/S0040-4020(03)00863-9
  17. Nina P. Grisant, Matthew S. Platz. Kinetics and spectroscopy of substituted phenylnitrenes. 2001,,, 255-304. https://doi.org/10.1016/S0065-3160(01)36006-9
  18. Raghoottama S. Pandurangl, Srinivasa R. Karra, Robert R. Kuntz, Wynn A. Volkert. Preservation of Immunoreactivity in the Photolabeling of the B72.3 Human Antibody. Photochemistry and Photobiology 1996, 64 (1) , 100-105. https://doi.org/10.1111/j.1751-1097.1996.tb02427.x
  19. E. W. Meijer, S. Nijhuis, F. C. B. M. Vroonhoven, E. E. Havinga. Poly-1,2-Azepines by the Photopolymerization of Phenyl Azides: A New Route to Processible Conducting Polymers. 1990,,, 115-131. https://doi.org/10.1007/978-94-009-2041-5_8
  20. E. W. Meijer, S. Nijhuis, E. E. Havinga. Polymers for Electronics and Photonics. 1989,,, 17-42. https://doi.org/10.1007/978-94-009-1115-4_2
  21. Mary Jennifer T. Young, Matthew S. Platz. Polyfluorinated aryl azides as photoaffinity labelling reagents; the room temperature CH insertion reactions of singlet pentafluorophenyl nitrene with alkanes. Tetrahedron Letters 1989, 30 (17) , 2199-2202. https://doi.org/10.1016/S0040-4039(00)99647-3
  22. Tsuei-Yun Liang, Gary B. Schuster. Photolysis of 3-nitrophenyl azide: Trapping the reactive intermediates. Tetrahedron Letters 1986, 27 (29) , 3325-3328. https://doi.org/10.1016/S0040-4039(00)84786-3
  23. Ronald E. Banks, Ismail M. Madany. Studies in azide chemistry. Part 13 [1]. Intermolecular insertion of azide-derived polyfluorinated aryl- and heteroaryl-nitrenes into ring CH bonds of 1,3, 5-trimethyl- and 1,3,5-trimethoxy-benzene. Journal of Fluorine Chemistry 1985, 30 (2) , 211-226. https://doi.org/10.1016/S0022-1139(00)80890-8
  24. G. G. Furin, G. F. Grebenshchikova, A. Ya. Lvova, V. M. Vlasov, G. G. Yakobson. Fluoroaromatic Compounds. 1985,,, 109-232. https://doi.org/10.1007/978-3-642-70207-5_3
  25. Peter A.S. Smith. Aryl and Heteroaryl Azides and Nitrenes. 1984,,, 95-204. https://doi.org/10.1016/B978-0-12-633480-7.50007-9
  26. P.A.S. Smith, C.D. Rowe, D.W. Hansen. Stereochemistry in the cyclization of -azidophenylalkenes to indoles. Tetrahedron Letters 1983, 24 (47) , 5169-5172. https://doi.org/10.1016/S0040-4039(00)88388-4
  27. E. F. V. Scriven. Current Aspects of the Solution Chemistry of Arylnitrenes. 1982,,, 1-54. https://doi.org/10.1007/978-1-4613-3192-6_1
  28. Lienhard Hoesch, Bruno Köppel. 1-Aryl- und 1-Alkyl-2-phthalimido-diazen-1-oxide, diacylierte Vertreter von trisubstituierten Triazen-1-oxiden: Bildung, Eigenschaften, Stereoisomerisierung und Fragmentierung. Helvetica Chimica Acta 1981, 64 (3) , 864-889. https://doi.org/10.1002/hlca.19810640325
  29. B. Iddon, O. Meth-Cohn, E. F. V. Scriven, H. Suschitzky, P. T. Gallagher. Entwicklungen in der Arylnitren-Chemie: Synthesen und Mechanismen. Angewandte Chemie 1979, 91 (12) , 965-982. https://doi.org/10.1002/ange.19790911205
  30. B. Iddon, O. Meth-Cohn, E. F. V. Scriven, H. Suschitzky, P. T. Gallagher. Developments in Arylnitrene Chemistry: Syntheses and Mechanisms [New synthetic methods (31)]. Angewandte Chemie International Edition in English 1979, 18 (12) , 900-917. https://doi.org/10.1002/anie.197909001
  31. Susan E. Carroll, Barry Nay, Eric F.V. Scriven, Hans Suschitzky. Decomposition of arylazides in piperidine: the effect of tetramethylethylenediamine on the nature of the products. Tetrahedron Letters 1977, 18 (11) , 943-946. https://doi.org/10.1016/S0040-4039(01)92798-4
  32. Rudolph A. Abramovitch, Stanley R. Challand. Pentafluoronitrosobenzene as a source of aryl nitrenc and as a radical trapping agent. Journal of Heterocyclic Chemistry 1973, 10 (4) , 683-685. https://doi.org/10.1002/jhet.5570100448
  33. R.A. Abramovitch. Nitrenes. 1973,,, 127-192. https://doi.org/10.1016/B978-0-12-485450-5.50008-7
  34. R.E. Banks, A. Prakash. New reactions of azidopentafluorobenzene; intermolecular ′insertions′ into n-h bonds. Tetrahedron Letters 1973, 14 (2) , 99-102. https://doi.org/10.1016/S0040-4039(01)95587-X
  35. R. A. ABRAMOVITCH, S. R. CHALLAND, E. F. V. SCRIVEN. ChemInform Abstract: MECHANISMUS DER INTERMOLEKULAREN AROMATISCHEN SUBSTITUTION DURCH ARYLNITRENE. Chemischer Informationsdienst 1972, 3 (20) , no-no. https://doi.org/10.1002/chin.197220119

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