Photocycloaddition reactions of 2-pyrones

CRC Handbook of: Organic Photochemistry and Photobiology, Second Edition

Volumn , Issue , 2003, Pages 82-1-82-19

  Shimo, Tetsuro ^a   Somekawa, Kenichi ^a  

^a KAGOSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85056316884     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (55)

1. Shusherina, N.P., Diene synthesis with 2-pyrones and 2-pyridones, Russ. Chem. Rev., 43, 851, 1974
2. Afarinkia, K., Vinader, V., Nelson, T.D. and Posner, G.H., Diels-Alder cycloadditions of 2-pyrones and 2-pyridones, Tetrahedron, 48, 9111, 1992.
3. Zimmerman, H.E., Grunewald, G.L., Paufler, R.M. and Sherwin, M.A., Synthesis and physical properties of barrelene, a unique Möbius-like model, J. Am. Chem. Soc., 91, 2330, 1969.
4. Schreiber, von J., Leimgruber, W., Pesaro, M., Schudel, P., Threlfall, T. and Eschenmoser, A., 65. Synthese des colchicins, Helv. Chim. Acta, 44, 540, 1961.
5. de Mayo, P. Ultraviolet photochemistry of simple unsaturated systems, in Advances in Organic Chemistry, 2, Raphael, R.A., Taylor, E.C. and Wynberg, H., Eds., Interscience, New York, 1960, 394
6. for further electrocyclic ring-opening of 2-pyrones see Pirkle, W.H. and McKendry, L.H., Photochemical reactions of 2-pyrone and thermal reactions of the 2-pyrone photoproducts, J. Am. Chem. Soc., 91, 1179, 1969
7. Chapman, O.L., McIntosh, C.L. and Pacansky, J., Photochemistry of α-pyrone in argon at 8°K, J. Am. Chem. Soc., 95, 244, 1973.
8. Corey, E.J. and Streith, J., Internal photoaddition reactions of 2-pyrone and N-methyl-2-pyridone: new synthetic approach to cyclobutadiene, J. Am. Chem. Soc., 86, 950, 1964.
9. de Mayo, P. and Yip, R.W., The photo-dimerisation of 2, 4-dimethylcoumalin: The synthesis of 1, 3, 5, 7-tetramethylcyclo-octatetraene, Proc. Chem. Soc., 84, 1964; for further photodimerisations of 2-pyrones see
10. Pirkle, W.H. and McKendry, L.H., The multiplicity of the reactive 2-pyrone excited states, Tetrahedron Lett., 5279, 1968.
11. Chapman, O.L., McIntosh, C.L. and Pacansky, J., Cyclobutadiene, J. Am. Chem. Soc., 95, 614, 1973.
12. Cram, D.J., Tanner, M.E. and Thomas, R., The taming of cyclobutadiene, Angew. Chem. Int. Ed. Engl., 30, 1024, 1991.
13. Hanifin, J. W. and Cohen, E., Some photochemical cycloadditions of coumarin, Tetrahedron Lett., 1419, 1966; for further photocycloaddition reactions of coumarins see
14. Pfoertner, K.-H., 84. Photoreaktionen von 3-substituierten cumarinen, Helv. Chim. Acta, 59, 834, 1976
15. Haywood, D.J., Hunt, R.G., Potter, C., J. and Reid, S.T., Photochemical transformations. Part 10. Photocycloaddition reactions of 4-hydroxycoumarin with cycloalkenes, J. Chem. Soc., Perkin Trans. 1, 2458, 1977
16. Naito, T., Nakayama, N. and Kaneko, C., A general synthetic method of 1, 2-dihydrocyclobuta[c]-coumarin and its 1-substituted derivatives, Chem. Lett., 423, 1981
17. Nonoyama, S., Yonezawa, N., Saigo, K., Hasegawa, M. and Iitaka, Y., Synthesis of dichlorocyclobuta[b]benzofuran-2a-carboxylic derivatives and 3-(trichloroethenyl)coumarin through cross photocycloadduct of coumarin and tetrachloroethylene, Bull. Chem. Soc. Jpn., 60, 349, 1987
18. Yasuda, M., Kishi, T., Goto, C., Satoda, H., Nakabayashi, K., Minami, T. and Shima, K., Efficient cross-photocycloadditions of 3-vinylcoumarins to olefins, Tetrahedron Lett., 33, 6465, 1992
19. Kobayashi, K., Suzuki, M. and Suginome, H., Photoinduced molecular transformations. Part 143. (2+2) Photoaddition of 3-hydroxy-1-benzopyran-2-one, 3-benzyloxycarbonyloxy-1-benzopyran-2-one and their 8-methoxy derivatives, with alkenes and formation of 1, 2-disubstituted 1, 2-dihydrofuro[2,3-c][1]benzopyran-4-ones by way of β-scission of cyclobutanoxyl radical generated from the resulting [2+2]-photoadducts, J. Chem. Soc., Perkin Trans. 1, 2837, 1993.
20. Takeshita, H., Kikuchi, R. and Shoji, Y., Synthetic photochemistry. II. The cycloaddition reaction of dehydroacetic acid with olefins, Bull. Chem. Soc. Jpn., 46, 690, 1973.
21. Shimo, T., Somekawa, K., Sato, M. and Kumamoto, S., The rmal and photoaddition reactions of methyl 2-pyrone-5-carboxylate with unsaturated compounds, Nippon Kagaku Kaishi, 1927, 1984
22. Chem. Abstr., 102, 149041w, 1985.
23. Shimo, T., Somekawa, K. and Kumamoto, S., Photochemical cycloadditions of 4, 6-dimethyl-2-pyrone to a few substituted ethylenes, Nippon Kagaku Kaishi, 394, 1983
24. Chem. Abstr., 99, 53539h, 1983.
25. Somekawa, K., Shimo, T., Yoshimura, H. and Suishu, T., Photo-cycloaddition reactions of 2-pyrones, Bull. Chem. Soc. Jpn., 63, 3456, 1990.
26. Shimo, T., Yamasaki, S., Date, K., Uemura, H. and Somekawa, K., Site-selective photocycloadditions of 2-pyrones with electron-poor olefins and the derivation from the cycloadducts, J. Heterocyclic Chem., 30, 419, 1993.
27. Shimo, T., Iwakiri, T. and Somekawa, K., Peri-selective photocycloadditions of methyl 2-pyrone-5-carboxylate with unsaturated cyclic ethers, J. Heterocyclic Chem., 29, 199, 1992.
28. Shimo, T., Yoshimura, H., Uemura, H., Somekawa, K. and Tsuge, O., Isolation of photo-Diels-Alder mono-adducts of 4, 6-dimethyl-2-pyrone and formation of cross-adducts, Heterocycles, 24, 3031, 1986.
29. Somekawa, K., Shimo, T. and Suishu, T., MO Analysis of photocycloaddition reactions of 2-pyrones, Bull. Chem. Soc. Jpn., 65, 354, 1992.
30. Suishu, T., Obata, T., Shimo, T. and Somekawa, K., Species specificity and regio-selectivities in the photocycloadditions of cyclic conjugated enones and heterocyclic conjugated dienones and their frontier MO analysis, Nippon Kagaku Kaishi, 167, 2000
31. Chem. Abstr., 132, 293339m, 2000.
32. Shimo, T., Yasuda, M., Tajima, J. and Somekawa, K., Intramolecular photoreactions of 4-(ω-alkenyloxy)-6-methyl-2-pyrones, J. Heterocyclic Chem., 28, 745, 1991.
33. Shimo, T., Tajima, J., Suishu, T. and Somekawa, K., Intramolecular photochemical reactions of 4-(ω-alkenyloxy)-6-methyl-2-pyrones having an alkoxycarbonyl group at the olefinic carbon chain, J. Org. Chem., 56, 7150, 1991.
34. Shimo, T., Matsuzaki, S. and Somekawa, K., Intramolecular photoreactions of 6-(ω-alkenyl)-4-methoxy-2-pyrones, J. Heterocyclic Chem., 31, 387, 1994.
35. Shimo, T., Ueda, S. and Somekawa, K., Photochemical behavior of 4-(ω-enyl)-and 4-(ω-dienyl)-2-pyrones, J. Heterocyclic Chem., 32, 341, 1995.
36. West, F.G., Chase, C., E. and Arif, A.M., Intramolecular [4+4]-photocycloadditions of 2-pyrones: n efficient approach to cyclooctanoid construction, J. Org. Chem., 58, 3794, 1993.
37. Chase, C.E., Bender, J. A. and West, F.G., Efficient construction of bi-and tricyclic cyclooctanoid systems via crossed [4+4]-photocycloadditions of pyrone-2-ones, Synlett, 1173, 1996.
38. van Meerbeck, M., Toppet, S. and de Schryver, F.C., Intramolecular photocycloaddition of 6, 6'-polymethylene-bis-(4-methyl-2-pyrone), Tetrahedron Lett., 2247, 1972.
39. Shimo, T., Ueda, S., Suishu, T. and Somekawa, K., Intramolecular photocycloadditions of 6, 6'-dimethyl-4, 4'-polymethylenedioxy-di-2-pyrones, J. Heterocyclic Chem., 32, 727, 1995.
40. Ramamurthy, V. and Venkatesan, K., Photochemical reactions of organic crystals, Chem. Rev., 87, 433, 1987
41. Ito, Y., Solid-state photoreactions in two-component crystals, Synthesis, 1, 1998.
42. Meng, J.-B., Zhu, Z.-L., Wang, R.-J., Yao, Z.-K., Ito, Y., Ihara, H. and Matsuura T., Selectivity in the solid-state photoreaction of 6-cyanouracils with aromatic hydrocarbons, Chem. Lett., 1247, 1990
43. Suzuki, T., Fukushima, T., Yamashita, Y. and Miyashi, T., An absolute asymmetric synthesis of the [2+2]-cycloadduct via single crystal-to-single crystal transformation by charge-transfer excitation of solid-state molecular complexes composed of arylolefins and bis[1,2,5]thiadiazolotetracyanoquinodimethane, J. Am. Chem. Soc., 116, 2793, 1994.
44. Rieke, R.D. and Copenhafer, R.A., Solid state organic photochemistry II. Photolysis of 4, 6-diphenyl-α-pyrone, Tetrahedron Lett., 879, 1971.
45. Sugiyama, N., Sato, T., Kataoka, H. and Kashima, C., The photoreaction of dehydroacetic acid, Bull. Chem. Soc. Jpn., 44, 555, 1971.
46. Ortmann, I., Werner, S., Krüger, C., Mohr, S. and Schaffner, K., Intermolecular π electron interactions made visible. Correlation of ground-and excited-state interactions with specific photoreactivities of isomorphously crystallized isoelectronic compounds, J. Am. Chem. Soc., 114, 5048, 1992 and references cited therein.
47. Obata, T., Shimo, T., Suishu, T. and Somekawa, K., Stereoselective photo [4+2]-cycloadditions of 2-pyrone-5-carboxylate with maleimides in the solid state and in solution, J. Heterocyclic Chem., 35, 1361, 1998.
48. Obata, T., Shimo, T., Yoshimoto, S., Somekawa, K. and Kawaminami, M., Peri-, site-and stereocontrolled photocycloaddition of 4-methoxy-6-methyl-2-pyrone with maleimide induced by the hydrogen bond and CT stacking in the solid state, Chem. Lett., 181, 1999.
49. Obata, T., Shimo, T., Yasutake, M., Shinmyozu, T., Kawaminami, M., Yoshida, R. and Somekawa, K., Remarkable interaction effects of molecular packing on site-and stereoselectivity in photocycloaddition of 2-pyrones with maleimide in the solid state, Tetrahedron, 57, 1531, 2001.
50. Shimo, T., Uezono, T., Obata, T., Yasutake, M., Shinmyozu, T. and Somekawa, K., x-ray and MO analysis of highly stereoselective solid-state photocycloadditions of 2-pyrones with maleimide, Tetrahedron, 58, 6111, 2002.
51. Somekawa, K., Imai, R., Furukido, R. and Kumamoto, S., Photoadducts of 2-pyridones with chloroethylenes and their derivatives, Bull. Chem. Soc. Jpn., 54, 1112, 1981
52. Yonezawa, N., Nonoyama, S., Saigo, K. and Hasegawa, M., Synthesis of dichlorocyclobuta[b]benzofuran-2a-carboxylic derivatives and 3-(trichlorovinyl)coumarin through the cross photocycloadduct of coumarin and tetrachloroethylene, J. Org. Chem., 50, 3026, 1985.
53. Shimo, T., Somekawa, K., Wakikawa, Y., Uemura, H., Tsuge, O., Imada, K. and Tanabe, K., Photoadducts of 4,6-dimethyl-and 4-methoxy-6-methyl-2-pyrones with chloroethylenes and their dehydrochlorination, Bull. Chem. Soc. Jpn., 60, 621, 1987.
54. Shimo, T., Date, K. and Somekawa, K., Novel transformations of two kinds of chlorinated photo [2+2]-cycloadducts of 2-pyrone-5-carboxylate, J. Heterocyclic Chem., 29, 387, 1992.
55. Shimo, T., Matsuo, K., Somekawa, K. and Tsuge, O., Diels-Alder reactions of cyclohexadienes derived from decarboxylation of photo [4+2]-cycloadducts between 4,6-dimethyl-2-pyrone and cyclic olefins, J. Heterocyclic Chem., 28, 549, 1991.