The “photochemical friedel-crafts acylation” of quinones: From the beginnings of organic photochemistry to modern solar chemical applications

CRC Handbook of: Organic Photochemistry and Photobiology, Second Edition

Volumn , Issue , 2003, Pages 88-1-88-45

  Oelgemöller, Michael ^a   Mattay, Jochen ^b  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b BIELEFELD UNIVERSITY   (Germany)

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EID: 84877719054     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (189)

1. Owton, W.M., The synthesis of quinones, J. Chem. Soc., Perkin Trans. 1, 2409-2420, 1999
2. Thomson, R.H., Naturally Occurring Quinones IV, Blackie, Glasgow, 1996
3. Thomson, R.H., The total synthesis of naturally occurring quinones, in Total Synthesis of Natural Products, Apsimon, J., Ed., John Wiley & Sons, New York, 1992
4. Thomson, R.H., Naturally Occurring Quinones III, Recent Advances, Chapman & Hall, London, 1987
5. Bérdy, J., Aszalos, A., Bostian, N., and McNitt, K.L., CRC Handbook of Antibiotic Compounds. Quinone and Similar Antibiotics, Vol. 3, CRC Press, Boca Raton, FL, 1980
6. Patai, S., Ed., The Chemistry of the Quinonoid Compounds, John Wiley & Sons, New York, 1974
7. Thomson, R.H., Naturally Occurring Quinones, 2nd ed., Academic Press, New York, 1971
8. Morton, R.A., Ed., Biochemistry of Quinones, Academic Press, New York, 1965.
9. Maruyama, K. and Osuka, A., Recent advances in the photochemistry of quinones, in The Chemistry of the Quinonoid Compounds, Patai, S. and Rappoport, Z., Eds., John Wiley & Sons, New York, 1988, Vol. 2, chap. 13, 759-878
10. Bruce, J.M., Photochemistry of quinones, in The Chemistry of the Quinonoid Compounds, Patai, S., Ed., John Wiley & Sons, New York, 1974, Vol. 1, chap. 9, 465-538
11. Bruce, J.M., Light-induced reactions of quinones, Quart. Rev., 21, 405-428, 1967
12. Hageman, H.J., Organisch photochemische Reaktionen; an funktionellen Gruppen; an der C=O-Doppelbindung; Chinone, in Methoden der organischen Chemie (Houben-Weyl), Müller, E., Ed., Thieme, Stuttgart, 1975, Vol. IV/5b: Photochemie, Part II, 941-985
13. Rubin, M.B., Photochemistry of o-quinones and α-diketones, Fortschr. Chem. Forsch., 13, 251-306, 1969
14. Mukherjee, T., Photo and radiation chemistry of quinones, Proc. Indian Natl. Sci. Acad., Part A, 66, 239-265, 2000.
15. For a number of excellent historical reviews, see (a) Roth, H.D., Die Anfänge der organischen Photochemie, Angew. Chem., 101, 1220-1234, 1989
16. The beginnings of organic photochemistry, Angew. Chem. Int. Ed. Engl., 28, 1193-1207, 1989
17. Roth, H.D., A brief history of photoinduced electron transfer and related reactions, Topics Curr. Chem., 156, 1-19, 1990
18. Roth, H.D., Twentieth century developments in photochemistry. Brief historical sketches, Pure Appl. Chem., 73, 395-403, 2001
19. Roth, H.D., Selected developments in the 20th century photochemistry: istorical sketches, EPA Newslett., 71, 37-57, 2001.
20. Klinger, H., Ueber das Isobenzil und die Einwirkung des Sonnenlichts auf einige organische Substanzen, Ber. Dtsch. Chem. Ges., 19, 1862-1870, 1886
21. Klinger, H., in Sitzungsber. Niederrhein. Ges. Natur Heilkde., 225-227, 1885
22. Klinger, H., in Sitzungsber. Niederrhein. Ges. Natur Heilkde., 224, 1883.
23. Klinger, H., Ueber die Einwirkung des Sonnenlichts auf organische Verbindungen, Justus Liebigs Ann. Chem., 249, 137-146, 1888
24. Klinger, H., in Sitzungsber. Niederrhein. Ges. Natur Heilkde., 31, 1888.
25. Klinger, H. and Standke, O., Ueber die Einwirkung des Sonnenlichts auf organische Verbindungen, Ber. Dtsch. Chem. Ges., 24, 1340-1346, 1891
26. Klinger, H. and Kolvenbach, W., Die Bildung von Acetohydrochinon aus Acetaldehyde und Benzochinon im Sonnenlicht, Ber. Dtsch. Chem. Ges., 31, 1214-1216, 1898
27. Klinger, H., Über Synthesen durch Sonnenlicht, Justus Liebigs Ann. Chem., 382, 211-221, 1911.
28. Dimroth, O. and Hilcken, V., Über Anthradichinone und Anthratrichinone, Ber. Dtsch. Chem. Ges., 54, 3050-3074, 1921.
29. Bargellini, G. and Monti, L., Reazione fra chinone e aldeide cinnamica sotto l’influenza della luce, Gazz. Chim. Ital., 60, 474-478, 1930.
30. Angeletti, A. and Migliardi, C., Reazione fra toluochinone e aldeide cinnamica per l’influenza della luce, Atti Accad. Sci. Torino, Cl. Sci. Fis. Mat. Nat., Series I, 70, 326-330, 1934/1935
31. Angeletti, A. and Baldini, V., Reazione fra toluochinone e aldeide benzoica per l’influenza della luce, Gazz. Chim. Ital., 64, 346-350, 1934.
32. Sircar, A.C. and Sen, S.C., Studied in the acenaphthenquinone series, J. Ind. Chem. Soc., 8, 605-612, 1931
33. Sircar, A.C. and Sen, S.C., Untersuchungen in der Acenaphthenchinonreihe, Chem. Zentralbl., 103, 1528, 1932.
34. Bogert, M.T. and Howells, H.P., The chemistry of the para-quinones. A contribution to the solution of the “Pechmann dyes” problem, J. Am. Chem. Soc., 52, 837-850, 1930.
35. Schönberg, A., in Präparative organische Photochemie, Springer, Berlin, 1958
36. Schönberg, A., Schenck, G.O. and Neumüller, O.A., in Preparative Organic Photochemistry, Springer, Berlin, 1968.
37. Schönberg, A. and Moubacher, R., Photo-reactions. Part IV. Photo-reaction between phenanthraquinone and aromatic aldehydes. A new passage from phenanthraquinone to fluorenone, J. Chem. Soc., 1430-1432, 1939
38. Schönberg, A. and Mustafa, A., Photochemical reactions in sunlight. XII. Reactions with phenanthraquinone, 9-arylxanthens and diphenyl triketone, J. Chem. Soc., 997-1000, 1947
39. Schönberg, A. and Mustafa, A., Reactions of non-enolizable ketones in sunlight, Chem. Rev., 40, 181-200, 1947
40. Schönberg, A., Latif, N., Moubasher, R., and Sina, A., Photochemical reactions in sunlight. XVI. (a) Photo-reduction of phenylglyoxylic acid. (b) Photoreactions between aldehydes and o-quinones. (c) Reactions between o-quinones and ethylenes in the dark and in the light, J. Chem. Soc., 1364-1369, 1951
41. Schönberg, A., Mustafa, A., and Zayed, S.M. A.D., Experiments with 1,2-benzophenazine-3,4-quinone. The rmochromic effects based on lactam-lactim tautomerism, J. Am. Chem. Soc., 75, 4302-4304, 1953
42. Schönberg, A., Awad, W.I., and Mousa, G.A., Photochemical reactions in sunlight. XVII. Experiments with 4-cyano-1,2-naphthoquinone, J. Am. Chem. Soc., 77, 3850-3852, 1955
43. Schönberg, A. and Sidky, M.M., Photochemical reactions in sunlight. XX. Photoreaction between benzaldehyde and khellinquinone, J Org. Chem., 22, 1698-1699, 1957.
44. See, for example, Pawellek, D., Ein-und mehrwertige Phenole; C. Trennung, Analytik und Stabilisierung; II. Analytik; a Chemische Methoden; 5. Farbreaktionen, in Methoden der organischen Chemie (Houben-Weyl), Müller, E., Ed., Thieme, Stuttgart, 1976, Vol. VI/1c: Phenole, Part II, 1204-1205.
45. Mustafa, A., Reactions in sunlight of (a) phenanthraquinone, retenequinone and chrysenequinone with ethylene retenequinone and chrysenequinone with aromatic aldehydes; and (c)o-formylbenzoic acid with iso-propyl alcohol, J. Chem. Soc., S83-S86, 1949
46. Mustafa, A., Reactions of 9-anthraldehyde in sunlight, Nature (London), 166, 108-109, 1950
47. Mustafa, A., Reactions in sunlight of certain diketones with ethylenes and aromatic aldehydes. Photopolymerisation of 9-anthraldehyde, J. Chem. Soc., 1034-1037, 1951
48. Mustafa, A., Harhash, A.H.E.H., Mansour, A.K.E., and Omran, S.M.A.E., Photochemical addition and photochemical dehydrogenation reactions in sunlight, J. Am. Chem. Soc., 78, 4306-4309, 1956
49. Mustafa, A., Mansour, A.K., and Shalaby, A.F.A.M., Photochemical reactions in sunlight. Experiments with benzo(h)quinoline-5,6-quinone, monoimine and monoxime derivatives in sunlight and in dark, J. Am. Chem. Soc., 81, 3409-3413, 1959
50. Mustafa, A., Mansour, A.K., and Zaher, H.A.A., Photochemical reactions in sunlight. Experiments with 2-N-phenyl-α,β-naphtho-1,2,3-triazolequinone and monoxime derivative in sunlight and in dark, J. Org. Chem., 25, 949-950, 1960.
51. Moore, R.F. and Waters, W.A., The photochemical addition of benzaldehyde to quinones, J. Chem. Soc., 238-240, 1953.
52. Rubin, M.B., Photochemical reactions of diketones. The 1,4-addition of ethers to 9,10-phenanthrenequinone, J. Org. Chem., 28, 1949-1952, 1963
53. Rubin, M.B. and Zwitkowits, P., Photochemical reactions of diketones. II. The 1,2-addition of substituted toluenes to 9,10-phenanthrenequinone, J. Org. Chem., 29, 2362-2368, 1964
54. Rubin, M.B. and Zwitkowits, P., Polar Effects in free radical reactions. The mechanism of photochemical addition of ethers and substituted toluenes to 9,10-phenanthrenequinone, Tetrahedron Lett., 2453-2457, 1965.
55. Badger, G.M., Pearce, R.S., and Pettit, R., Polynuclear heterocyclic systems. II. Hydroxy-derivatives, J. Chem. Soc., 3204-3207, 1951
56. for a general review on imine-enamine tautomerizations, see Kurasawa, Y., Takada, A., and Kim, H.S., Tautomerism and isomerism of heterocycles [2], Heterocycles, 41, 2057-2093, 1995.
57. Awad, W.I. and Hafez, M.S., Studies on 4-substituted-β-naphthoquinones, J. Am. Chem. Soc., 80, 6057-6060, 1958.
58. Schenck, G.O. and Koltzenburg, G., Zur Photochemie des Chloranils, Angew. Chem., 66, 475, 1954
59. Schenck, G.O. and Koltzenburg, G., Zur Photochemie der Chinone, Naturwiss., 41, 452, 1954.
60. Scharf, H.-D., Fleischhauer, J., and Aretz, J., Apparative Hilfsmittel; Allgemeines zur Ausführung photochemischer Reaktionen, in Methoden der organischen Chemie (Houben-Weyl), Müller, E., Ed., Thieme, Stuttgart, 1975, Vol. IV/5a: Photochemie, Part I, 41-89
61. Schenck, G.O., Probleme präparativer Photochemie, Angew. Chem., 64, 12-23, 1952.
62. For some selected reviews on Photo-Fries rearrangements, see (a) Martin, R., Uses of the Fries rearrangement for the preparation of hydroxyarylketones. A review, Org. Prep. Proc. Int., 24, 373-435, 1992
63. Pfau, M. and Julliard, M., Reactions photochimiques des esters aromatiques, Bull. Chem. Soc. Fr., 785-802, 1977
64. Bellus, D., Photo-Fries rearrangement and related photochemical [1, j]-shifts (j = 3,5,7) of carbonyl and sulfonyl groups, Adv. Photochem., 8, 109-159, 1971.
65. Bruce, J.M. and Cutts, E., The mechanism of the light-induced reaction between 1,4-benzoquinone and acetaldehyde, J. Chem. Soc., Chem. Commun., 2-3, 1965
66. Bruce, J.M. and Cutts, E., Light-induced and related reactions of quinones. I. The mechanism of formation of acetylquinol from 1,4-benzoquinone and acetaldehyde, J. Chem. Soc. (C), 449-458, 1966
67. Bruce, J.M., and Ellis, J.N., Light-induced and related reactions of quinones. II. Reactions involving chloranil and acetaldehyde, J. Chem. Soc. (C), 1624-1627, 1966
68. Bruce, J.M., Creed, D., and Ellis, J.N., Lightinduced and related reactions of quinones. IV. Reactions of some p-quinones with aliphatic and aromatic aldehydes, J. Chem. Soc. (C), 1486-1490, 1967
69. Bruce, J.M. and Dawes, K., Light-induced and related reactions of quinones. V. Substituent effects in light-induced reactions between p-quinones and aldehydes, J. Chem. Soc. (C), 645-648, 1970
70. Bruce, J.M. and Chaudhry, A.-U.-H, Light-induced and related reactions of quinones. IX. t-Butyl-1,4-benzoquinones, J. Chem. Soc., Perkin Trans. 1, 372-379, 1972
71. Bruce, J.M. and Chaudhry, A.-U.-H., Light-induced and related reactions of quinones. XI. 4,4'-Diphenoquinones, J. Chem. Soc., Perkin Trans. 1, 295-297, 1974.
72. Chatgilialoglu, C., Crich, D., Komatsu, M., and Ryu, I., Chemistry of acyl radicals, Chem. Rev., 99, 1991-2069, 1999
73. Caronna, T. and Minisci, F., The chemistry of acyl radicals, Rev. React. Species Chem., 1, 263-318, 1976.
74. For a number of redox potentials of quinones, see (a) Ulrich, H. and Richter, R., Die para-Chinone der Benzol-und Naphthalin-Reihe; C. Charakterisierung und Bestimmung von p-Chinonen. II. Durch physikalische Methoden Polarographie (Oxidationspotential), in Methoden der organischen Chemie (Houben-Weyl), Müller, E. and Grundmann C., Eds., Thieme, Stuttgart, 1976, Vol. VII/3a: Chinone, Part I, 730-732
75. Chambers, J.Q., Electrochemistry of quinones, in The Chemistry of the Quinonoid Compounds, Patai, S., Ed., John Wiley & Sons, New York, 1974, Vol. 1, chap. 14, 737-791
76. Peover, M.E., A polarographic investigation into the redox behaviour of quinones: he roles of electron affinity and solvent, J. Chem. Soc., 4540-4549, 1962.
77. Formosinho, S.J. and Arnaut, L.G., Excited-state proton transfer reactions. II. Intramolecular reactions, J. Photochem. Photobiol. A: Chem., 75, 21-48, 1993
78. Rommel, E. and Wirz, J., The photoenol tautomer of 5-methyl-1,4-naphthoquinone, Helv. Chim. Acta, 60, 38-42, 1977
79. Chiang, Y., Kresge, A.J., Hellrung, B., Schünemann, P., and Wirz, J., Flash photolysis of 5-methyl-1,4-naphthoquinone in aqueous solution: kinetics and mechanism of photoenolization and of enol trapping, Helv. Chim. Acta, 80, 1106-1121, 1997.
80. Orlando Jr., C.M., Mark, H., Bose, A.K. and Manhas, M.S., Photoreactions. IV. Photolysis of t-butyl-substituted p-benzoquinones, J. Am. Chem. Soc., 89, 6527-6532, 1967
81. Orlando, Jr., C.M., Mark, H., Bose, A.K., and Manhas, M.S., Photoreactions.V. Mechanism of the photorearrangement of alkyl-p-benzoquinones, J. Org. Chem., 33, 2512-2516, 1968
82. Farid, S., Biradical trapping with sulphur dioxide: sulphinic acids from the photoreaction of t-butyl-p-benzoquinone with sulphur dioxide, J. Chem. Soc., Chem. Commun., 73-74, 1971
83. Farid, S., Photolysis of tbutyl-p-quinones: competing 1,4-and 1,5-dipolar cycloadditions of the photoproduct to nitriles and ketones, J. Chem. Soc., Chem. Commun., 303-304, 1970.
84. Maruyama, K., Takuwa, A., Otsuki, T., and Kako, S., Syntheses of 9-acyloxy-10-hydroxyphenanthrenes by photochemical reaction, Bull. Inst. Chem. Res., Kyoto Univ., 50, 348-353, 1972
85. Maruyama, K. and Takahashi, G., Photochemical reaction of 9,10-phenanthrenequinone with glyoxals, Chem. Lett., 295-298, 1973
86. Maruyama, K. and Takuwa, A., 3-Acyl-1,2-naphthoquinols from the photo-induced reaction of 1,2-naphthoquinone derivatives with aliphatic aldehydes, Chem. Lett., 471-474, 1974
87. Maruyama, K., Miyazawa, T., and Kishi, Y., A novel type of adducts in the photochemical reactions of o-chloranil with aldehydes, Chem. Lett., 721-724, 1974
88. Maruyama, K. and Miyagi, Y., Photo-induced condensation reaction of p-quinones with aldehydes, Bull. Chem. Soc. Jpn., 47, 1303-1304, 1974
89. Maruyama, K., Otsuki, T., and Naruta, Y., Photochemical reaction of 9,10-phenanthrenequinone with hydrogen donors. Behavior of radicals in solution as studied by CIDNP, Bull. Chem. Soc. Jpn., 49, 791-795, 1976
90. Maruyama, K. and Naruta, Y., Syntheses of α-and β-lapachones and their homologues by way of photochemical side chain introduction to quinone, Chem. Lett., 847-850, 1977
91. Maruyama, K., Sakurai, H., and Otsuki, T., The addition reaction of acyl radicals to 9,10-phenanthrenequinone in the presence of the corresponding aldehydes. A support for the in-cage mechanism of the photochemical reaction of 9,10-phenanthrenequinone with aldehydes, Bull. Chem. Soc. Jpn., 50, 2777-2779, 1977
92. Maruyama, K., Takuwa, A., and Soga, O., Photochemical reaction of 1,2-naphthoquinone with arylacetaldehydes. Products and their intramolecular isomerization, Chem. Lett., 1097-1100, 1979
93. Maruyama, K., Takuwa, A., Matsukiyo, S., and Soga, O., Mechanism of light-induced reductive acetylation of 1,2-naphthoquinone with acetaldehyde, J. Chem. Soc., Perkin Trans. 1, 1414-1419, 1980
94. Takuwa, A., Iwamoto, H., Soga, O., and Maruyama, K., The formation of acetylcatechol in the photochemical reaction of o-benzoquinones with acetaldehyde, Bull. Chem. Soc. Jpn., 55, 3657-3658, 1982
95. Takuwa, A., Soga, O., and Maruyama, K., The photochemical reaction of 1,2-naphthoquinone with hydrogen donors. An explanation of the coupling sites of alkyl and acyl radicals to 1,2-naphthosemiquinone radical, J. Chem. Soc., Perkin Trans. 2, 409-411, 1985.
96. Takuwa, A., The photochemical reaction of 1,2-naphthoquinone with aldehydes. II. The photoaddition reactions of aliphatic aldehydes to 1,2-naphthoquinones, Bull. Chem. Soc. Jpn., 49, 2790-2799, 1976
97. Takuwa, A., The photochemical reaction of 1,2-naphthoquinone with aldehydes. III. The reactions with aromatic aldehydes and α,β-unsaturated aliphatic aldehydes, Bull. Chem. Soc. Jpn., 50, 2973-2981, 1977
98. Takuwa, A. and Ryoji, K., Convenient synthesis of 3-acyl and 3-alkyl-1,2-naphthoquinones, Bull. Chem. Soc. Jpn., 63, 623-625, 1990.
99. Kraus, G.A. and Kirihara, M., Quinone photochemistry. A general synthesis of acylhydrochinones, J. Org. Chem., 57, 3256-3257, 1992
100. Kraus, G.A. and Liu, P., Benzophenone-mediated conjugated additions of aromatic aldehydes to quinones, Tetrahedron Lett., 35, 7723-7726, 1994
101. Kraus, G.A., Kirihara, M., and Wu, Y., A photochemical alternative to certain Friedel-Crafts reactions, in Benign by Design. Alternative Synthetic Design for Pollution Prevention, Anastas, P.T. and Farris, C.A., Eds., ACS Symposium Series 577, American Chemical Society, Washington D.C., 76-83, 1994
102. Kraus, G.A., Maeda, H., Lui, P., Melekhov, A., and Lu, Y., A photochemical alternative to certain Friedel-Crafts reactions, in Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes, Anastas, P.T. and Williamson, T.C., Eds., Oxford University Press, Oxford, 1998, chap. 4, 72-86
103. Pacut, R., Grimm, M.L., Kraus, G.A., and Tanko, J.M., Photochemistry in supercritical carbon dioxide. The benzophenone-mediated addition of aldehydes to α,β-unsaturated carbonyl compounds, Tetrahedron Lett., 42, 1415-1418, 2001.
104. Kobayashi, K., Suzuki, M., Takeuchi, H., Konishi, A., Sakurai, H., and Suginome, H., Photoinduced molecular transformations. 146. Photoacylation and photoalkylation of 2-arylamino-and 2-alkylamino-1,4-naphthoquinones, J. Chem. Soc., Perkin Trans. 1, 1099-1104, 1994
105. Kobayashi, K., Yoneda, K., Uchida, M., Matsuoka, H., Morikawa, O., and Konishi, H., An improved method for the preparation of 4,7-dioxo-4,7-dihydrobenzo[b]thiophene-2-carboxylates from 2-acyl-1,4-benzoquinones and mercaptoacetates, Heterocycles, 55, 2423-2430, 2001
106. Kobayashi, K., Matsunaga, A., Mano, M., Morikawa, O., and Konishi, H., A new route to benzo[b]xanthene-6,11,12-trione derivatives based on the photoinduced o-hydroxybenzoylation of 1,4-naphthoquinone, Heterocycles, 57, 1915-1918, 2002
107. Kobayashi, K., Ogata, T., Miyamoto, K., Morikawa, O., and Konishi, H., Synthesis of benzo[1,2-b: 5,4-b’]dithiophene-4,8-dione derivatives, Heterocycles, 60, 1689-1695, 2003.
108. Tachikawa, N., Photochemically induced regio-selective acylation of quinones, Chem. Express, 1, 587-590, 1986
109. Tachikawa, N., Photochemically induced regio-selective acylation of quinolinequinones, Chem. Express, 3, 33-36, 1988.
110. Mattay, J., Hoffmann, R., Langer, K., Oelgemöller, M., and Schiel C., Untersuchungen zur Nutzung solarer Energien zur Synthese von Wirkstoffen und Zwischenprodukten, in Solare Chemie und Solare Materialforschung -Ergebnisse der ersten Förderphase des Schwerpunktes 5 in der nordrhein-westfälischen Arbeitsgemeinschaft Solar, Becker, M. and Funken K.-H., Eds., Verlag C.F. Müller, Heidelberg, 1997, 234-241
111. Schiel, C., Oelgemöller, M., and Mattay, J., Regioselective photoacylation of substituted naphthoquinones, J. Inf. Rec., 24, 257-260, 1998
112. Schiel, C., Oelgemöller, M., and Mattay, J., Photoacylation of electron-rich quinones: an application of the photo-Friedel-Crafts reaction, Synthesis, 1275-1279, 2001
113. Schiel, C., Oelgemöller, M., Ortner, J., and Mattay, J., Green photochemistry: the solar-chemical photo-Friedel-Crafts acylation of quinones, Green Chem., 3, 224-228, 2001
114. Oelgemöller, M., Schiel, C., Mattay, J., and Fröhlich, R., The photo-Friedel-Crafts acylation of 1,4-naphthoquinones, Eur. J. Org. Chem., 2465-2474, 2002
115. Oelgemöller, M., Schiel, C., Ortner, J., and Mattay, J., The solarchemical “Photo-Friedel-Crafts acylation” of quinones; in AG Solar Nordrhein-Westfalen --Solare Chemie und Solare
116. Materialforschung -Förderzeitraum 1995-2001, AG Solar NRW, Projektträger ETN, Ed., Forschungszentrum Jülich GmbH, 2002, chap. 2.2, CD-ROM, ISBN 3-89336-306-8
117. Schiel, C., Photochemische Acylierung von Chinonen und ihre solartechnische Anwendung, Ph.D. thesis, University of Bielefeld, 2002
118. Mattay, J., Von der Laborsynthese zur Solarchemie, Chem. unserer Zeit, 36, 98-106, 2002.
119. For some selected examples of the green photochemistry concept, see (a) Griesbeck, A.G. and Bartoschek, A., Sustainable photochemistry: solvent-free singlet oxygen-photooxygenation of organic substrates embedded in porphrin-loaded polystyrene beads, J. Chem. Soc., Chem. Commun., 1594-1595, 2002
120. Albini, A., Fagnoni, M., and Mella, M., Environment-friendly organic synthesis. The photochemical approach, Pure Appl. Chem., 72, 1321-1326, 2000
121. Griesbeck, A.G., Kramer, W., and Oelgemöller, M., Photoinduced decarboxylation reactions -radical chemistry in water, Green Chem., 1, 205-207, 1999
122. Covell, C., Gilbert, A., and Richter, C., Sun light induced regio-and stereo-specific (2π+2π) cycloaddition of arylethenes to 2-substituted-1,4-naphthoquinones, J. Chem. Res. (S), 316-317, 1998.
123. Esser, P., Pohlmann, B., and Scharf, H.-D., The photochemical synthesis of fine chemicals with sunlight, Angew. Chem. Int. Ed. Engl., 33, 2009-2023, 1994
124. Funken, K.-H. and Ortner, J., Technologies for the solar photochemical and photocatalytic manufacture of specialities and commodities: review, Z. Phys. Chem., 213, 99-105, 1999
125. Funken, K.-H., Ortner, J., Riffelmann, K.-J., and Sattler, C., New developments in solar photochemistry, J. Inf. Rec., 24, 61-68, 1998
126. Lede, J., and Pharabod, F., Chimie solaire dans le monde et en france, Entropie, 204, 47-55, 1997.
127. Ferreira, M.A., King, T.J., Sadaquat, A., and Thomson, R.H., Naturally occurring quinones. 27. Sesquiterpenoid quinones and related compounds from hibiscus elatus: crystal structure of hibiscone C (gmelofuran), J. Chem. Soc., Perkin Trans. 1, 249-256, 1980; for intramolecular reactions of 1,4 benzoquinones
128. Bruce, J.M. and Creed, D., Light-induced and related reactions of quinones. Part VI. Reactions of some p-quinones carrying formyl groups. J. Chem. Soc. (c), 649-653, 1970.
129. Kim, A.R., Kyeong, J.K., Shim, S.C., and Kim, S.S., Formation of 1,5-diketones from the photoaddition of 1,3-diphenyl-1,3-propanedione to p-benzoquinones, Bull. Korean Chem. Soc., 18, 1125-1126, 1998
130. Chang, J.A., Kim, A.R., and Kim, S.S., Photochemical formation of 1,5-diketones from dibenzoylmethane and o-quinones, Bull. Korean Chem. Soc., 19, 917-919, 1998
131. Kim, S.S., Lim, J.S., Lee, J.M., and Shim, S.C., Photochemical formation of 1,5-diketones from dibenzoylmethane and some quinones, Bull. Korean Chem. Soc., 20, 531-534, 1999
132. Kim, S.S., Chang, J.A., Kim, A.R., Mah, Y.J., Kim, H.J., and Kang, C., Photochemical formation of 3-methoxycyclohex-2-en-1-ones from 1,3-cyclohexanedione and 2-allyl-3-hydroxycyclohex-2-en-1-one in methanol in the presence of quinones, J. Photosci., 7, 111-114, 2000.
133. Abdulla, K.A., Abdul-Rahman, A.L., Al-Hamdany, R., and Al-Saigh, Z.Y., Preparation and light induced reactions of substituted 1,4-benzoquinone, J. Prakt. Chem., 324, 498-504, 1982; for more detailed studies on this transformation
134. Bruce, J.M. and Knowles, P., Light-induced and related reactions of quinones. Part III. Light-induced reactions of some monosubstituted 1,4-benzoquinones, J. Chem. Soc. (c), 1627-1634, 1966
135. Bruce, J.M., Creed, D., and Dawes, K., Light-induced and related reactions of quinones. Part VII. Cleavage and isomerization of some (1-hydroxyalkyl)-1,4-benzoquinones. J. Chem. Soc. (c), 2244-2252, 1971
136. Bruce, J.M., Chaudhry, A.-u.-h., and Dawes, K., Light-induced and related reactions of quinones. Part X. Further studies with hydroxymethyl-, vinyl-, and (2-ethoxycarbonylethyl)-1,4-benzoquinones, J. Chem. Soc., Perkin Trans. 1, 288-294, 1974.
137. Maruyama, K., Iwamoto, H., Soga, O., Takuwa, A., and Osuka, A., Photochemical reaction of 2-alkenoyl-3-alkoxy-1,4-benzoquinones. Formation of 5H-pyrano[4,3,2-de][1,3]benzodioxin derivatives, Chem. Lett., 1675-1678, 1985
138. Maruyama, K., Iwamoto, H., Soga, O., Takuwa, A., and Osuka, A., Photochemical reaction of 2-alkenoyl-1,4-quinones. Formation of chromone derivatives, Chem. Lett., 595-598, 1985
139. Maruyama, K., Iwamoto, H., Soga, O., and Takuwa, A., Photochemical reaction of 2-alkenoyl-3,5-dimethyl-1,5-benzoquinones with alcohol, Chem. Lett., 1343-1346, 1984
140. Maruyama, K., Muraoka, M., and Naruta, Y., Photo-oxygenation of 2-alkenoyl-1,4-quinones by atmospheric oxygen. Formation of stable cyclic peroxides, J. Chem. Soc., Chem. Comm., 1282-1284, 1980
141. Miyagi, Y., Maruyama, K., and Yoshimoto, S., The chemical conversion of the photo-dimer of 2-acetyl-5-methyl-1,4-benzoquinone. The determination of the regiochemistry of the dimer, Bull. Chem. Soc. Jpn., 53, 2962-2965, 1980
142. Maruyama, K. and Narita, N., Photochemical dimerization of 2-acyl-1,4-benzoquinones in the presence of rose bengal, J. Org. Chem., 45, 1421-1424, 1980
143. Maruyama, K. and Narita, N., Photochemical reaction sensitized by dyes in heterogeneous phase, Chem. Lett., 1211-1212, 1979
144. Miyagi, Y., Maruyama, K., Ishii, H., Mizuno, S., Kakudo, M., Tanaka, N., Matsuura, Y., and Harada, S., The photochemical dimerization of 2-acyl-1,4-quinones, Bull. Chem. Soc. Jpn., 52, 3019-3026, 1979
145. Maruyama, K., Narita, N., and Miyagi, Y., Photochemical reaction of 2-acetyl-1,4-benzoquinone in the presence of rose bengal, Chem. Lett., 1033-1034, 1978
146. Miyagi, Y., Kitamura, K., Maruyama, K., and Chow Y.L., Photochemical dimerization of 2-acyl-1,4-quinones, Chem. Lett., 33-36, 1978.
147. Yonezawa, N., Hino, T., and Ikeda, T., New approaches in Friedel-Crafts type carbon-carbon bond formation using novel types of Friedel-Crafts mediators, in Recent Research Developments in Organic Chemistry, Pandalai, S.G., Ed., Transworld Research Network, Trivandrum, 1998, Vol. 1, 213-223
148. Olah, G.A., Definition and scope: acylation (including halogenation and related reactions), in Friedel-Crafts and Related Reactions, Olah, G.A., Ed., Wiley, New York, 1963, Vol. 1, chap. 2, Section IV, 91-169
149. Gore, P.H., Aromatic ketone synthesis, in Friedel-Crafts and Related Reactions, Olah, G.A., Ed., Wiley, New York, 1964, Vol. 3, chap. 31, 1-381
150. Kurosawa, E., Quinones. I. The syntheses of acetyl-p-benzoquinone derivatives and 2-acetylnaphthoquinone, Bull. Chem. Soc. Jpn., 34, 300-304, 1961.
151. Kraus, G.A. and Melekhov, A., A direct route to acylhydroquinones from α-keto acids and α-carboxamido acids, Tetrahedron Lett., 39, 3957-3960, 1998.
152. Boyer, J.L., Krum, J.E., Myers, M.C., Fazal, A.N., and Wigal, C.T., Synthetic utility and mechanistic implications of the Fries rearrangement of hydroquinone diesters in boron trifluoride complexes, J. Org. Chem., 65, 4712-4714, 2000
153. Amin, G.C. and Shah, N.M., 2,5-Dihydroxyacetophenone, Org. Synth., 42, 42-43, 1948.
154. Sharam, P.K. and Khanna, R.N., Photo-Fries rearrangement: rearrangement of benzoyloxy compounds, Monatsh. Chem., 116, 353-356, 1985
155. Escobar, C., Fariña, F., Martinez-Utrilla, R., and Paredes, M.C., Polycyclic hydroxyquinones. 1. Photo-Fries rearrangement of polyacetoxynaphthalenes; Application to the synthesis of some acetylnaphthazarin derivatives, J. Chem. Res. (S), 266-267, 1977
156. J. Chem. Res. (M), 3154-3168, 1977
157. Park, K.K., Lee, H.J., Kim, E.H., and Kang, S.K., Facile synthesis and photo-Fries rearrangement of 2-benzoyl-4-benzoyloxyphenol leading to dibenzoyldihydroxybenzene derivatives, J. Photochem. Photobiol A: Chem., 159, 17-21, 2003.
158. For an introduction on green chemistry, see Tundo, P., Anastas, P., Black, D. StC., Breen, J., Collins, T., Memoli, S., Miyamoto, J., Polyakoff, M., and Tumas, W., Synthetic pathways and processes in green chemistry. Introductory overview, Pure Appl. Chem., 72, 1207-1228, 2000.
159. Brimble, M.A., Synthetic studies towards pyranonaphthoquinone antibiotics, Pure Appl. Chem., 72, 1635-1639, 2000
160. Brimble, M.A., Nairn, M.R., and Prabaharan, H., Synthetic strategies towards pyranonaphthoquinone antibiotics, Tetrahedron, 56, 1937-1992, 2000
161. Brimble, M.A., Duncalf, L.J., and Nairn, M.R., Pyranonaphthoquinone antibiotics -isolation, structure and biological activity, Nat. Prod. Rep., 16, 267-281, 1999
162. de Koning, C.B., Giles, R.G.F., and Green, I.R., Naphthopyranquinones. Confirmation of the structures of the ventiloquinones E, G and J by synthesis, J. Chem. Soc., Perkin Trans. 1, 2743-2748, 1991
163. Kraus, G.A. and Shi, J., A versatile intermediate for the synthesis of pyranoquinone antibiotics, J. Org. Chem., 55, 1105-1106, 1990
164. Uno, H., Allylation of 2-alkanoyl 1,4-quinones with allysilanes and allystannanes. Efficient synthesis of pyranonaphthoquinone antibiotics, J. Org. Chem., 51, 350-358, 1986.
165. Kraus, G.A. and Maeda, H., A direct preparation of 1,4-benzodiazepines. The synthesis of medazepam and related compounds via a common intermediate, Tetrahedron Lett., 35, 9189-9190, 1994.
166. Thurston, D.E. and Bose, D.S., Synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines, Chem. Rev., 94, 433-465, 1994
167. Schütz, H., Benzodiazepines II. A Handbook, Springer-Verlag, Berlin, 1989
168. Roth, H.J., Kleemann, A., and Beisswenger, T., Pharmaceutical Chemistry, Drug Synthesis, Vol. 1, Ellis Horwood, Chichester, 1988
169. Mohiuddin, G., Reddy, P.S., Ahmed, K., and Ratnam, C.V., Recent advantages in the synthesis of annelated 1,4-benzodiazepines, Heterocycles, 24, 3489-3530, 1986.
170. Couladouros, E.A., Strongilos, A.T., Papageorgiou, V.P., and Plyta, Z.F., A new efficient route for multigram asymmetric synthesis of alkannin and shikonin, Chem.-Eur. J., 8, 1795-1803, 2002
171. Papageorgiou, V.P., Assimopoulou, A.N., Couladouros, E.A., Hepworth, D., and Nicolaou, K.C., The chemistry and biology of alkannin, shikonin and related naphthazarin natural products, Angew. Chem. Int. Ed. Engl., 38, 270-300, 1999
172. Nicolaou, K.C. and Hepworth, D., Concise and efficient total syntheses of alkannin and shikonin, Angew. Chem. Int. Ed. Engl., 37, 839-841, 1998
173. Tanoue, Y., Terada, A., and Sugyo-, Y., Cycloshikonin and its derivatives. A synthetic route of shikonin, J. Org. Chem., 52, 1437-1439, 1987.
174. Kobayashi, K., Uchida, M., Watanabe, S., Takanohashi, A., Tanmatsu, M., Morikawa, O., and Konishi, H., Synthesis of 1-amino and 1-hydroxy-9,10-anthraquinone derivatives based on reaction sequences between 2-acetyl-1,4-naphthoquinone and enamines, Tetrahedron Lett., 41, 2381-2384, 2000.
175. Uno, H., Masumoto, A., Honda, E., Nagamachi, Y., Yamaoka, Y., and Ono, N., Intramolecular aldol-type condensation between side chains of naphthoquinones: biomimetic synthesis of 1,6-and 1,8-dihydroxyanthraquinones, J. Chem. Soc., Perkin Trans. 1, 3189-3189, 2001
176. Uno, H., Nagamachi, Y., Honda, E., Masumoto, A., and Ono, N., Regioselective preparation of 1,6-and 1,8-dihydroxy-9,10-anthraquinones from the common intermediates: synthesis of aloesaponarin I and K1115A, Chem. Lett., 1014-1015, 2000.
177. Nguyen Van, T., Kesteleyn, B., and De Kimpe, N., Synthesis of 1,3-disubstituted naphtho[2,3-c]pyran-5,10-diones, Tetrahedron, 57, 4213-4219, 2001.
178. Kobayashi, K., Takanohashi, A., Watanabe, S., Morikawa, O., and Konishi, H., One-pot synthesis of isoquinoline-5,8-dione derivatives from acylquinones and enamines, Tetrahedron Lett., 41, 7657-7660, 2000.
179. Kubo, A. and Saito, N., Synthesis of isoquinolinequinone antibiotics, in Studies in Natural Products Chemistry. Vol. 10: Stereoselective Synthesis, Rahman, A.-U., Ed., Elsevier, Amsterdam, 1992, Part F, 77-145
180. Ozturk, T., Alkaloids containing an isoquinolinequinone unit, in Alkaloids: hemistry and Biology, Cordell, G.A., Ed., Academic, San Diego, Vol. 53, 119-238, 2000.
181. Naruta, Y., Nishigaichi, Y., and Maruyama, K., Tandem Michael/Diels-Alder addition as a new strategy toward tetracyclic systems: synthesis of 11-deoxyanthracyclinones, J. Org. Chem., 53, 1192-1199, 1988
182. Uno, H., Naruta, Y., and Maruyama, K., Syntheses of (±)-aklavinones. Application of the stereocontrolled “zipper” bicyclo-cyclization reaction, Tetrahedron, 40, 4741-4725, 1984.
183. Arcamone, F., Doxorubicin, Academic Press, New York, 1981
184. El Khadem, H.S., Ed., Anthracycline Antibiotics, Academic Press, New York, 1982.
185. Konieczny, M.T., Horowska, B., Kunikowski, A., Konopa, J., Wierzba, K., Yamada, Y., and Asao, T., Synthesis and reactivity of 5,8-dihydroxythioflavone derivatives, J. Org. Chem., 64, 359-364, 1999.
186. Harborne, J.B., Ed., Flavonoids: Advances in Research, Chapman & Hall, London, 1993.
187. Ueno, Y., Shiraki, H., Koshitani, J., and Yoshida, T., The photochemical reaction of 5Hbenzo[ a]phenothiazin-5-ones with aldehydes, Synthesis, 313-314, 1980.
188. For other “Photo-Friedal-Crafts reactions”, see (a) Martens, J., Praefcke, K., and Schulze, U., Intramoleulare Photo-Friedel-Crafts-Reaktionen; ein neues Syntheses-Prinzip für Heterocyclen, Synthesis, 532-533, 1976
189. Bryce-Smith, D., Deshpande, R., Gilbert, A., and Grzonka, J., Acidcatalysis of photochemical reactions, Chem. Commun., 561-562, 1970.