Photoredox, photodecarboxylation, and photo-retro-Aldol chemistry of p-nitrobiphenyls

Photochemical and Photobiological Sciences

Volumn 1, Issue 6, 2002, Pages 384-394

  Morrison, James ^a   Osthoff, Hans ^a   Wan, Peter ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROBIPHENYL DERIVATIVE; ANION; BENZENE; BENZENE DERIVATIVE; BENZYL DERIVATIVE; BIPHENYL; NITROGEN; UNCLASSIFIED DRUG;

ACIDITY; ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; CONJUGATION; CONTROLLED STUDY; DECARBOXYLATION; ELECTRON TRANSPORT; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; POLARIZATION; PRIORITY JOURNAL; QUANTUM CHEMISTRY;

EID: 0042831279     PISSN: 1474905X     EISSN: None     Source Type: Journal    
DOI: 10.1039/b201087a     Document Type: Article

References (24)

1. D. Döpp, Photochemical Reactivity of the Nitro Group, in CRC Handbook of Organic Photochemistry and Photobiology, W. M. Horspool and P.-S. Song (eds.), CRC Press, Boca Raton, Florida, 1995, Ch. 81, pp. 1019-1062;
2. D. Döpp, Reactions of Aromatic Nitro Compounds via Excited Triplet States, Top. Curr. Chem., 1975, 55, 49-85;
3. Y. L. Chow, Photochemistry of Nitro and Nitroso Compounds, in The Chemistry of Amino, Nitro, and Nitroso Compounds and Their Derivatives, S. Patai (ed.), Wiley, New York, 1982, pp. 181-290;
4. H. A. Morrison, The Photochemistry of the Nitro and Nitroso Groups, in The Chemistry of the Nitro and Nitroso Groups, H. Feuer (ed.), Wiley, New York, 1969, pp. 165-213.
5. R. W. Binkley and T. W. Flechtner, Photoremovable Protecting Groups, in Synthetic Organic Photochemistry, W. M. Horspool (ed.), Plenum Press, New York, 1984, pp. 375-423.
6. P. Wan and S. Muralidharan, Structure and Mechanism in the Photo-Retro-Aldol Type Reactions of Nitrobenzyl Derivatives. Photochemical Heterolytic Cleavage of C-C Bonds, J. Am. Chem. Soc., 1988, 110, 4336-4345;
7. see also: P. Wan, and S. Muralidharan, J. Am. Chem. Soc., 1990, 112, 4611, for error correction.
8. J. D. Margerum and C. T. Petrusis, The Photodecarboxylation of Nitrophenylacetate Ions, J. Am. Chem. Soc., 1969, 91, 2467-2472;
9. B. B. Craig, R. G. Weiss and S. J. Atherton, Picosecond and Nanosecond Laser Photolyses of p-Nitrophenylacetate in Aqueous Media. A Photoadiabatic Decarboxylation Process?, J. Phys. Chem., 1987, 91, 5906-5912;
10. B. B. Craig and S. J. Atherton, Kinetics and Spectral Properties of the Photogenerated p-Nitrobenzyl Carbanion in Aqueous Media, J. Chem. Soc., Perkin Trans. 2, 1988, 1929-1935.
11. P. Wan and K. Yates, Photoredox Chemistry of Nitrobenzyl Alcohols in Aqueous Solution. Acid and Base Catalysis of Reaction, Can. J. Chem., 1986, 64, 2076-2086.
12. T. C. Werner, Use of Fluorescence to Study Structural Changes and Solvation Phenomenon in Electronically Excited Molecules, in Modern Fluorescence Spectroscopy, Vol. 2, E. Wehry (ed.), Plenum Press, New York, 1976, pp. 277-317;
13. A. Imamura and R. Hoffmann, The Electronic Structure and Torsional Potentials in Ground and Excited States of Biphenyl, Fulvalene, and Related Compounds, J. Am. Chem. Soc., 1968, 90, 5379-5385;
14. H. E. Zimmerman and D. S. Crumrine, Duality of Mechanism in Photoracemization of Optically Active Biphenyls. Mechanistic and Exploratory Photochemistry. LXV, J. Am. Chem. Soc., 1972, 94, 498-506;
15. K. Mislow and A. J. Gordon, Photoracemization of Biphenyls, J. Am. Chem. Soc., 1963, 85, 3521-3522;
16. C.-G. Huang, K. Beveridge and P. Wan, Photocyclization of 2-(2′-Hydroxyphenyl)benzyl Alcohol and Derivatives via o-Quinonemethide Type Intermediates, J. Am. Chem. Soc., 1991, 113, 7676-7684.
17. M. Maus, W. Rettig, D. Bonafoux and R. Lapouyade, Photoinduced Intramolecular Charge Transfer in a Series of Differentially Twisted Donor-Acceptor Biphenyls as Revealed by Fluorescence, J. Phys. Chem. A, 1999, 103, 3388-3401;
18. S. Delmond, J.-F. Létard, R. Lapouyade and W. Rettig, Photoinduced Intramolecular Charge Transfer in Planar vs Twisted Donor-Acceptor Terphenyls, J. Photochem. Photobiol., A, 1997, 105, 135-148.
19. J. Morrison, H. Osthoff and P. Wan, Enhanced Photoreactivity of the Nitrobiphenyl Chromophore, Photochem. Photobiol. Sci., 2002, 1, 22-23.
20. S. Muralidharan and P. Wan, ESR Studies of Photogenerated Nitrobenzyl Carbanions in Aqueous Solution, J. Photochem. Photobiol., A, 1991, 57, 191-206.
21. S. L. Murov, I. Carmichael and G. L. Hug, Handbook of Photochemistry, 2nd edn., M. Dekker, New York, 1993.
22. T. R. Schatz, R. Kobetic and P. Piotrowiak, Probing Preferential Solvation and Ion Aggregation with Charge Transfer Triplet States of Aromatic Amino-Nitro Compounds, J. Photochem. Photobiol., A, 1996, 105, 249-254.
23. R. B. Miller and S. Duger, Stoichiometric Synthesis of Unsymmetrical Mononitrobiphenyls via the Palladium-Catalyzed Cross-Coupling of Arylboronic Acids with Arylbromides, Organometallics, 1984, 3, 1261-1263.
24. R. S. Bly, K. K. Tse and R. K. Bly, The Preparation and Acetolysis of Some [π-Phenylchromium Tricarbonyl] Benzyl p-Toluene-sulfonates and Their Noncomplexed Analogs. A Search for σ-π Delocalization, J. Organomet. Chem., 1976, 117, 35-54.