Position-dependent fragmentation mechanism for radical anions of fluorinated benzoates

Journal of Fluorine Chemistry

Volumn 188, Issue , 2016, Pages 171-176

  Mashkantsev, Dmitry E ^a,b   Beregovaya, Irina V ^a   Shchegoleva, Lyudmila N ^a  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

Author keywords

C F bond cleavage; Fluoroarene radical anions; Potential energy surfaces; Pseudorotation; Regioselectivity

Indexed keywords

EID: 84978395245     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2016.07.002     Document Type: Article

References (19)

1. [1] Shteingarts, V.D., Recent advances in practice and theory of polyfluoroarene hydrodehalogenation. J. Fluorine Chem. 128 (2007), 797–805.
2. [2] Platonov, V.E., Vinogradov, A.S., Krasnov, V.I., Polyfluoroarenes and Zn: hydrogenolysis reactions, synthesis and chemical properties of polyfluoroaromatic organozinc compounds. Fluorine Notes, 66, 2009.
3. [3] Kuehnel, M.F., Lentz, D., Braun, T., Synthesis of fluorinated building blocks by transition-metal-mediated hydrodefluorination reactions. Angew. Chem. Int. Ed. 52 (2013), 3328–3348.
4. [4] Borovkov, V., Stass, D., Bagryansky, V., Molin, Y., Study of spin-correlated radical ion pairs in irradiated solutions by optically detected EPR and related techniques. Lund, A., Shiotani, M., (eds.) Applications of EPR in Radiation Research, 2014, Springer International Publishing, 629–663.
5. [5] Shchegoleva, L.N., Beregovaya, I.V., Potential energy surface as a key to understanding the structure and properties of short-living radical ions of cyclic organic molecules. Int. J. Quantum Chem. 116 (2016), 161–173.
6. [6] Clarke, D.D., Coulson, C.A., The dissociative breakdown of negative ions. J. Chem. Soc. A 2 (1969), 169–172.
7. [7] Beregovaya, I.V., Shchegoleva, L.N., Potential energy surface and dissociative cleavage of chlorobenzene radical anion. Chem. Phys. Lett. 348 (2001), 501–506.
8. [8] Konovalov, V.V., Laev, S.S., Beregovaya, I.V., Shchegoleva, L.N., Steingarts, V.D., Tsvetkov, Yu.D., Bilkis, I., Fragmentation of radical anions of polyfluorinated benzoates. J. Phys. Chem. A 104 (2000), 352–361.
9. [9] Steppard, W.A., Sharts, C.M., Organic Fluorine Chemistry. 1969, W. A. Benjamin Inc., New York.
10. [10] Pierini, A.B., Vera, D.M., Ab initio evaluation of intramolecular electron transfer reactions in halobenzenes and stabilized derivatives. J. Org. Chem. 68 (2003), 9191–9199.
11. [11] Beregovaya, I.V., Vysotskii, V.P., Shchegoleva, L.N., Monomolecular decay of anion-radicals of isomeric chlorobenzonitriles. Quantum chemical analysis. J. Struct. Chem. 47 (2006), 211–219.
12. [12] Beregovaya, I.V., Shchegoleva, L.N., Pseudorotation as a mechanism for intramolecular electron density transfer. Fragmentation of the octafluoronaphthalene radical anion. J. Fluorine Chem. 163 (2014), 1–6.
13. [13] Senaweera, S.M., Singh, A., Weaver, J.D., Photocatalytic hydrodefluorination: facile access to partially fluorinated aromatics. J. Am. Chem. Soc. 136 (2014), 3002–3005.
14. [14] Freeman, P.K., Srinivasa, R., Photochemistry of polyhaloarenes. 6. Fragmentation of polyfluoroarene radical anions. J. Org. Chem. 52 (1987), 252–256.
15. [15] Schmidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Cordon, M.S., Jensen, J.J., Koseki, S., Matsunaga, N., Nguyen, K.A., Su, S., Windus, T.L., Dupuis, M., Montgomery, J.A., General atomic and molecular electronic structure system. J. Comput. Chem. 14 (1993), 1347–1363.
16. [16] Schaftenaar, G., Noordik, J.H., Molden: a pre- and post-processing program for molecular and electronic structures. J. Comput. Aided Mol. Des. 14 (2000), 123–134.
17. [17] Shchegoleva, L.N., Beregovaya, I.V., Schastnev, P.V., Potential energy surface of C6F6radical anion. Chem. Phys. Lett. 312 (1999), 325–332.
18. [18] Beregovaya, I.V., Shchegoleva, L.N., Potential energy surfaces of fluorobenzene radical anions. Int. J. Quantum Chem. 88 (2002), 481–488.
19. [19] Laev, S.S., Reductive Defluorination of Fluorinated Benzoic Acids, PhD Thesis. 1999, Novosibirsk, Novosibirsk Institute of Organic Chemistry, SB, RAS, Russia.