Photo-fries reaction and related processes

CRC Handbook of: Organic Photochemistry and Photobiology, Second Edition

Volumn , Issue , 2003, Pages 42-1-42-11

  Miranda, Miguel Angel ^a   Galindo, Francisco ^b  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

^b UNIVERSITAT JAUME I   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85056330574     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (101)

1. Anderson, J. C. and Reese, C. B., Photo-induced Fries rearrangement, Proc. Chem. Soc. London, 217, 1960.
2. Kharasch, M. S., Stampa, G., and Nudenberg, W., Photochemicalpara rearrangement of phenyl ethers, Science, 116, 309, 1952
3. Carroll, F. A. and Hammond, G. S., Mechanisms of photochemical reactions in solution. 72. Electronic pathways in photodissociation of 3-methyl-1-phenoxybut-2-ene, J. Am. Chem. Soc., 94, 7151, 1972
4. Adam, W., FischerH., Hansen, H.-J., Heimgartner, H., Schmid, H., and Waespe, H.-R., CIDNP evidence for divergent behavior of singlet and triplet radical pair encounters in photo-Claisen rearrangement, Angew. Chem. Int. Ed. Engl., 12, 662, 1973
5. Haga, N. and Takayanagi, H., Mechanisms of the photochemical rearrangement of diphenyl ethers, J. Org. Chem., 61, 735, 1996
6. Galindo, F., Miranda, M. A., and Tormos, R., Coupling of phenoxy and alkyl radicals derived from the photolysis of phenol/ketone pairs: an intermolecular approach to the photo-Claisen rearrangement, J. Photochem. Photobiol. A: Chem., 117, 17, 1998
7. (f), DeCosta, D. P., Bennett, A., Pincock, A. L., Pincock, J. A., and Stefanova, R., Photochemistry of aryl tert-butyl ethers in methanol: the effect of substituents on an excited state cleavage reaction, J. Org. Chem., 65, 4162, 2000.
8. Stenberg, V. I., Photo-Fries reaction and related arrangements, Org. Photochem., 1, 127, 1967.
9. Bellus, D., Photo-Fries reaction and related photochemical [1, j]-shifts (j = 3,5,7) of carbonyl and sulfonyl groups, Adv. Photochem., 8, 109, 1971.
10. Martin, R., Uses of the Fries rearrangement for the preparation of hydroxyarylketones: a review, Org. Prep. Proc. Int., 24, 369, 1992.
11. Miranda, M. A. and Galindo, F., The photo-Fries rearrangement, in Molecular and Supramolecular Photochemistry, Vol. 9, Ramamurthy, V. and Schanze, K. S., Eds., Marcel Dekker, New York, 2003.
12. Gritsan, N. P., Tsentalovich, Y. P., Yurkovskaya, A. V., and Sagdeev, R., J. Phys. Chem., 100, 4448, 1996.
13. Kalmus, C. E. and Hercules, D. M., Mechanisticstudy of photo-Fries rearrangement, Tetrahedron Lett., 16, 1575, 1972
14. Kalmus, C. E. and Hercules, D. M., Mechanisticstudy of photo-Fries rearrangement of phenyl acetate, J. Am. Chem. Soc., 96, 449, 1974
15. Arai, T., Tobita, S., and Shizuka, H., Directmeasurements of the rates of 1,3-sigmatropic and 1,5-sigmatropic hydrogen shifts in the photo-Fries rearrangements of phenyl acetate, Chem. Phys. Lett., 223, 521, 1994
16. Arai, T., Tobita, S., and Shizuka, H., Tunnelingeffects on the 1,3-sigmatropic and 1,5-sigmatropic hydrogen shifts in the ground-state of photo-Fries rearranged intermediates of phenyl acetate studied by laser flash-photolysis, J. Am. Chem. Soc., 117, 3968, 1995.
17. Beck, S. M. and Brus, L. E., Transientintermediates in the photo-Fries isomerization of phenyl acetate via spontaneous Raman spectroscopy, J. Am. Chem. Soc., 104, 1805, 1982.
18. Rosenthal, I., Mosoba, M. M., and Riesz, P., Spintrapping with 2-methyl-2-nitrosopropane: photochemistry of carbonyl-containing compounds. Methyl radical formation from dimethyl sulfoxide, Can. J. Chem., 60, 1468, 1982.
19. Nakagaki, P., Hiramatsu, M., Watanabe, T., Tanimoto, Y., and Nagakura, S., Magneticisotope and external magnetic field effects upon the photo-Fries rearrangement of 1-naphthyl acetate, J. Phys. Chem., 89, 3222, 1985.
20. 13C) isotope effects in the photo-Fries rearrangement of 4-methoxyphenyl acetate, J. Org. Chem., 52, 3815, 1987.
21. Jiménez, M. C., Miranda, M. A., Scaiano, J. C., and Tormos, R., Two-photon processes in the photo-Claisen and photo-Fries rearrangements. Direct observation of dienic ketenes generated by photolysis of transient cyclohexa-2,4-dienones, J. Chem. Soc., Chem. Commun., 1487, 1997.
22. Jiménez, M. C., Leal, P., Miranda, M. A., and Tormos, R., Norrishtype-I photoreaction in the presence of phenols. An intermolecular photo-Fries rearrangement, J. Chem. Soc., Chem. Commun., 2009, 1995.
23. Grimme, S., The oreticalinvestigation on the photodissociation of carbon oxygen bonds in aromatic-compounds, Chem. Phys., 163, 313, 1992.
24. García, H., Miranda, M. A., Roquet-Jalmar, M. F., and Martínez-Utrilla, R., Influence of enol acetylation on the photo-Fries rearrangement of an ortho-acylaryl benzoate, Liebigs Ann. Chem., 2238, 1982.
25. García, H., Martínez-Utrilla, R., Mirada, M. A., and Roquet-Jalmar, M. F., Intra-and intermolecular photoreactions of o-benzoyloxyacetophenone derivatives, J. Chem. Res., (S), 350, 1982.
26. García, H., Miranda, M. A., and Primo, J., The photo-Fries rearrangement of acetoxyacetophenones using cyclic acetals as carbonyl blocking groups in the presence of potassium carbonate: an improved procedure for the synthesis of diacylphenols. J. Chem. Res., (S), 100, 1986.
27. García, H., Martínez-Utrilla, R., and Miranda, M. A., Cyclicacetals as carbonyl blocking groups in the photo-Fries rearrangement of acyl substituted aryl esters, Tetrahedron, 41, 3131, 1985.
28. Crouse, D. J., Hurlbut, S. L., and Wheeler, D. M. S., Photo-Fries rearrangements of 1-naphthyl esters in the synthesis of 2-acylnaphthoquinones, J. Org. Chem., 46, 374, 1981.
29. Fariña, F., Martínez-Utrilla, R., and Paredes, M. C., Polycyclichydroxyquinones. VIII. Preparation of acetylhydroxynaphthazarines by photo-Fries rearrangement: a convenient synthesis of spinochrome A, Tetrahedron, 38, 1531, 1982.
30. Greenland, H., Pinhey, J. T., and Sternhell, S. The photochemistry of 2-acetoxynaphthalen-1(2H)-ones, J. Chem. Soc., PerkinTrans. 1, 1789, 1986.
31. Kulshrestha, S. K., Dureja, P., and Mukerjee, S. K., Photo-induced reactions. IV. Studies on photo-Fries migration of some coumarins, Ind. J. Chem., 23B, 1064, 1984.
32. Miranda, M. A., Primo, J., and Tormos, R., Photochemistry of 7-acetoxybenzopyran derivatives: ynthesis of eupatoriochromene and encecalin, Tetrahedron, 45, 7593, 1989.
33. Chan, A. C. and Chilliard, P. R., Regioselectivity of the photo-Fries rearrangement in acetoxyindoles, Tetrahedron Lett., 30, 6483, 1989.
34. Ishii, H., Sekiguchi, F., and Ishikawa, T., Studieson the chemical constituents of rutaceous plants. XLI. Absolute configuration of rutaretin methyl ether, Tetrahedron, 37, 285, 1981.
35. Marriot, K.-S. C., Anderson, M., and Jackson, Y. A., Synthesis of a 2,3-dimethoxyrotenonoid, Heterocycles, 55, 91, 2001
36. Suau, R., Valpuesta, M., and Torres, G., Photochemical-synthesis of 7,8-dioxygenated isoquinoline alkaloids, Tetrahedron Lett., 36, 1315, 1995
37. Magnus, P. and Lescop, C., Photo-Fries rearrangement for the synthesis of the diazonamide macrocycle, Tetrahedron Lett., 42, 7193, 2001
38. Okada, K., Suzuki, R., and Yokota, T., Synthesis and root growthpromoting activity of capillarol and its derivatives, Biosci. Biotechnol. Biochem., 63, 257, 1999.
39. 3H)-furanones, Monatsh. Chem., 120, 863, 1989.
40. Martínez-Utrilla, R. and Miranda, M. A., Indirecthydroquinone succinoylation via a photo-Fries rearrangement: application to the synthesis of enol lactones, Tetrahedron Lett., 21, 2281, 1980.
41. Alvaro, M., García, H., Miranda, M. A., and Primo, J., Neighbouringgroup participation in the photolysis of aryl esters of unsaturated 1,4-dicarboxylic acids, Recl. Trav. Chim. Pays-Bas, 105, 233, 1986.
42. Alvaro, M., García, H., Iborra, S., Miranda, M. A., and Primo, J., Newphotochemical approaches to the synthesis of chromones, Tetrahedron, 43, 143, 1987.
43. Miranda, M. A., Primo, J., and Tormos, R., Influence of the stereochemistry on the rate of cyclization of cis and trans o-hydroxyaryl alkenyl ketones: mechanistic implications, Tetrahedron, 43, 2323, 1987.
44. Miranda, M. A., Primo, J., and Tormos, R., A new synthesis of precocene II and precocene III based on the photo-Fries rearrangement of a sesamol ester, Heterocycles, 32, 1159, 1991.
45. Miranda, M. A., Primo, J., and Tormos, R., A new synthesis of 4-chromanones, Heterocycles, 19, 1819, 1982.
46. Miranda, M. A., Primo, J., and Tormos, R., Studieson the synthesis of precocenes: the photo-Fries rearrangement of esters of α,β-unsaturated carboxylic acids and meta-oxygenated phenols, Heterocycles, 27, 673, 1988.
47. García, H., Iborra, S., Miranda, M. A., and Primo, J., Application of the photo-Fries rearrangement of aryl dihydrocinnamates to the synthesis of flavonoids, Heterocycles, 23, 1983, 1985.
48. García, H., Iborra, S., Miranda, M. A., and Primo, J., Photolysis of cyclic acetals of aryl benzoyl acetates as the key step in a new synthesis of flavones, Heterocycles, 24, 2511, 1986.
49. García, H., Iborra, S., Miranda, M. A., and Primo, J., 6-Endo-dig versus 5-exo-dig ring closure in o-hydroxyaryl phenylethynyl ketones: a new approach to the synthesis of flavones and aurones, J. Org. Chem., 51, 4432, 1986.
50. Lewis, J. R. and Paul J. G., Oxidativecoupling. 11. Approaches to the synthesis of bikaverin, J. Chem. Soc., Perkin Trans. 1, 770, 1981.
51. Katagiri, N., Nakano, J., and Kato, T., Synthesis of bikaverin, J. Chem. Soc., Perkin Trans. 1, 2710, 1981.
52. Díaz-Mondéjar, M. R. and Miranda, M. A., 2'-Acetoxy-2-hydroxy-5-methoxybenzophenone: photochemical synthesis, transacylation and cyclization to 2-methoxyxanthone, Tetrahedron, 38, 1523, 1982.
53. Díaz-Mondéjar, M. R. and Miranda, M. A., Photolysis of 2-aryloxy-or 2-arylthio-1,3-benzodioxan-4-ones, Heterocycles, 22, 1125, 1984.
54. Belled, C., Miranda, M. A., and Simón-Fuentes, A., Fototransposición de Fries en derivados de tiosalicilato de fenilo: una nueva aproximación a la síntesis de tioxantonas, An. Quím., 85C, 39, 1989.
55. Belled, C., Miranda, M. A., and Simón-Fuentes, A., Fototransposición de Fries de esters fenólicos de los ácidos antranílico y N-acetilantranílico: aplicaciones a la síntesis de heterociclos, An. Quím., 86C, 431, 1990.
56. Baldwin, J. E., Rules for ring closure, J. Chem. Soc., Chem. Commun., 734, 1976.
57. Avnir, D., de Mayo, P., and Ono, I., Biphasicphotochemistry: the photo-Fries rearrangement on silica gel, J. Chem. Soc., Chem. Commun., 1109, 1978.
58. Ohara, M. and Watanabe, K., Selectivephotochemical Fries rearrangement of phenyl acetate in the presence of β-cyclodextrin, Angew. Chem. Int. Ed. Engl., 14, 820, 1975.
59. Chênevert, R. and Voyer, N., Photochemicalrearrangement of phenyl benzoate in the presence of cyclodextrins and amylose, Tetrahedron Lett., 25, 5007, 1984.
60. Syamala, M. S., Rao, B. N., and Ramamurthy, V., Modification of photochemical reactivity by cyclodextrin complexation: product selectivity in photo-Fries rearrangement, Tetrahedron, 44, 7234, 1988.
61. Veglia, A. V., Sánchez, A. M., and de Rossi, R. H., Change of selectivity in the photo-Fries rearrangement of phenyl acetate induced by β-cyclodextrin, J. Org. Chem., 55, 4083, 1990.
62. Veglia, A. V. and de Rossi, R. H., Beta-cyclodextrin effects on the photo-Fries rearrangement of aromatic alkyl esters, J. Org. Chem., 58, 4941, 1993.
63. Xie, R.-Q., Liu, Y.-C., and Lei, X.-G., The photo-Fries rearrangement of alpha-naphthyl acetate in cyclodextrin and micelle, Res. Chem. Intermed., 18, 61, 1992
64. Banu, H. S., Pitchumani, K., and Srinivasan, C., Effect of cyclodextrin complexation on photo-Fries rearrangement of naphthyl esters, Tetrahedron, 55, 9601, 1999.
65. Pitchumani, K., Velusamy, P., Manickam, M. C., Durai, M. C., and Srinivasan, C., Influence of cyclodextrin complexation on photo-Fries rearrangement of sulfonyl derivatives, Proc. Indian Acad. Sci., Chem. Sci., 106, 49, 1994
66. Pitchumani, K., Manickam, M. C., Durai, M. C., and Srinivasan, C., Modification of photochemical behavior upon cyclodextrin complexation. Photo-Fries rearrangement of sulfonate esters, Ind. J. Chem., Sect. B, 32B, 1074, 1993.
67. Singh, A. K. and Sonar, S. N., Photorearrangement of aryl esters in micellar medium, Synth. Commun., 15, 1113, 1985.
68. Suau, R., Torres, G., and Valpuesta, M., The photo-Fries rearrangement of 2,5-disubstituted phenyl acetates, Tetrahedron Lett., 36, 1311, 1995.
69. García, H., Primo, J., and Miranda, M. A., The photo-Fries rearrangement in the presence of potassium carbonate: a convenient synthesis of ortho-hydroxyacetophenones, Synthesis, 901, 1985.
70. Tung, C.-H. and Xu, X.-H., Selectivityin the photo-Fries reaction of phenyl phenylacetates included in a nafion membrane, Tetrahedron Lett., 40, 127, 1999.
71. Cui, C., Wang, X., and Weiss, R. G., Investigation of the photo-Fries rearrangements of two 2-naphthyl alkanoates by experiment and theory: comparison with the acid-catalyzed reactions, J. Org. Chem., 61, 1962, 1996
72. Baldvins, J. E., Cui, C., and Weiss, R. G., Investigations of cylindrical reaction cavities from ordered phases of alkyl alkanoates and their influence on some Norrish-Yang and photo-Fries reactions, Photochem. Photobiol., 63, 726, 1996.
73. Hoyle, C. E., Shah, H., and Nelson, G. L., Photochemistry of bisphenol-A based polycarbonate: he effect of the matrix and early detection of photo-Fries product formation, J. Polym. Sci., Part A: Polym. Chem., 30, 1525, 1992.
74. Gu, W. Q., Hill, A. J., Wang, X. C., Cui, C. X., and Weiss, R. G., Photorearrangements of five 1-and 2-naphthyl acylates in three unstretched and stretched polyethylene films. Does reaction selectivity correlate with free volumes measured by positron annihilation lifetime spectroscopy?, Macromolecules, 33, 7801, 2000
75. Gu, W. and Weiss, R. G., Extractingfundamental photochemical and photophysical information from photorearrangements of aryl phenylacylates and aryl benzyl ethers in media comprised of polyolefinic films, J. Photochem. Photobiol. C: Photochem. Rev., 2, 117, 2001.
76. Gu, W. Q., Bi, S. G., and Weiss, R. G., Photo-Fries rearrangements of 1-naphthyl esters in the glassy and melted states of poly(vinyl acetate). Comparisons with reactions in less polar polymers and low-viscosity solvents, Photochem. Photobiol. Sci., 1, 52, 2002.
77. Pitchumani, K., Warrier, M., and Ramamurthy, V., Remarkableproduct selectivity during photo-Fries and photo-Claisen rearrangements within zeolites, J. Am. Chem. Soc., 118, 9428, 1996
78. Pitchumani, K., Warrier, M., and Ramamurthy, V., Utility of zeolitic medium in photo-Fries and photo-Claisen rearrangements, Res. Chem. Intermed., 25, 623, 1999
79. Pitchumani, K., Warrier, M., Cui, C., Weiss, R. G., and Ramamurthy, V., Photo-Fries reaction of naphthyl esters within zeolites, Tetrahedron Lett., 37, 6251, 1996
80. Balkus, J. K., Khanmamedova, A. K., and Woo, R., Friesrearrangement of acetanilide over zeolite catalysts, J. Mol. Catal. A: Chem., 134, 137, 1998
81. Gu, W., Warrier, M., Ramamurthy, V., and Weiss, R. G., Photo-Fries reactions of 1-naphthyl esters in cation-exchanged zeolite Y and polyethylene media, J. Am. Chem. Soc., 121, 9467, 1999.
82. Tung, C.-H. and Ying, Y.-M., Photochemistry of phenyl phenylacetates adsorbed on pentasil and faujasite zeolites, J. Chem. Soc., Perkin. Trans. 2, 1319, 1997
83. Tung, C.-H., Wu, L.-Z., Zhang, L.-P., Li, H.-Ru., Yi, X.-Y., Song, K., Xu, M., Yuan, Z.-Y., Guan, J.-Q., Wang, H.-W., Ying, Y.-M., and Xu, X.-H., Microreactor-controlled selectivity in organic photochemical reactions, Pure Appl. Chem., 72, 2289, 2000.
84. Andrew, D., Des Islet, B. T., Margaritis, A., and Weedon, A. C., Photo-Fries rearrangement of naphthyl acetate in supercritical carbon-dioxide: chemical evidence for solvent-solute clustering, J. Am. Chem. Soc., 117, 6132, 1995.
85. Allen, N. S., Photostabilizingaction of ortho-hydroxy aromatic compounds: a critical review, Polym. Photochem., 3, 167, 1983.
86. Ranby, B. and Rabek, J. F., Photodegradation, Photo-oxidation and Photostabilization of Polymers, Wiley, New York, 1975.
87. Rivaton, A., Sallet, D., and Lemaire, J., The photochemistry of bisphenol A polycarbonate reconsidered, Polym. Photochem., 3, 463, 1983.
88. Torikai, A., Murata, T., and Fueki, K., Photo-induced reactions of polycarbonate studied by ESR, viscosity and optical absorption measurements, Polym. Photochem., 4, 255, 1984.
89. Rivaton, A., Mailhot, B., Soulestin, J., Varghese, H., and Gardette, J. L., Comparison of the photochemical and thermal degradation of bisphenol-A polycarbonate and trimethylcyclohexane-polycarbonate, Polym. Degrad. Stab., 75, 17, 2002.
90. Rivaton, A., Mailhot, B., Soulestin, J., Varghese H., and Gardette, J. L., Influence of the chemical structure of polycarbonates on the contribution of crosslinking and chain scissions to the photothermal ageing, Eur. Polym. J., 38, 1349, 2002.
91. David, M., Creed, D., Griffin, A. C., Hoyle, C. E., and Venkataram, K., Photochemicalcrosslinking of main-chain liquid-crystalline polymers containing cinnamoyl groups, Makromol. Chem. Rapid Commun., 10, 391, 1989.
92. David, M., Creed, D., Griffin, A. C., Hoyle, C. E., and Venkataram, K., Chromophoreaggregation and concomitant wavelength-dependent photochemistry of a main-chain liquid-crystalline poly(arylcinnamate), J. Am. Chem. Soc., 112, 4049, 1990.
93. Hoyle, C. E. and Kim, K. J., Photolysis of aromatic diisocyanate-based polyurethanes in solution, J. Polym. Sci., Part A: Polym. Chem., 24, 1879, 1986.
94. Hoyle, C. E., Chawla, C. P., and Kim K. J., The effect of flexibility on the photodegradation of aromatic diisocyanate-based polyurethanes J. Polym. Sci., Part A: Polym. Chem., 26, 1295, 1988.
95. Wilhelm, C., Rivaton, A., and Gardette, J.-L., Infraredanalysis of the photochemical behaviour of segmented polyurethanes. 3. Aromatic diisocyanate based polymers, Polymer, 39, 1223, 1998
96. Liaw, D. J., Lin, S. P., and Liaw, B. Y., Photolysis of bisphenol-based polyurethanes in solution, J. Polym. Sci., Part A: Polym. Chem., 37, 1331, 1999.
97. Lo, J., Lee, N. S., and Pearce, E. M., Photo-Fries rearrangement of fluorene-based polyacrylates, J. Appl. Polym. Sci., 29, 35, 1984.
98. Holden, D. A., Jordan, K., and Safarzadeh-Amiri, A., Studies of polymer photostabilization using fluorescence spectroscopy: photochemistry of naphthyl methacrylate copolymers, Macromolecules, 19, 895, 1986.
99. Wang, Z., Holden, D. A., and McCourt, F. R. W., Generation of nonrandom chromophore distributions by the photo-Fries reaction of 2-naphthyl acetate in poly(methyl methacrylate), Macromolecules, 23, 3773, 1990.
100. Tessier, T. G., Frechet, J. M. J., Willson, C. G., and Ito, H., The photo-Fries rearrangement and its use in polymeric imaging systems, Am. Chem. Soc. Symp. Ser., 266, 269, 1984.
101. Frechet, J. M. J., Tessier, T. G., Willson, C. G., and Ito, H., Poly[p-(formyloxy)styrene]: synthesis and radiation-induced decarbonylation, Macromolecules, 18, 317, 1985.