Abstract
Activity in the photochemistry of α-diketones has continued unabated in the past decade. In addition to special attention to absorption and emission spectra, photoelectron spectroscopy has been applied widely. Areas of recent emphasis include (1) cyclobutene- and (2) cyclobutanediones, (3) bridged cyclohexenediones, and (4) reactions in the presence of oxygen, particularly epoxidation of olefins. The more venerable aspects such as inter- and intramolecular hydrogen atom abstraction reactions and additions to multiple bonds continue to receive attention. A considerable number of examples of synthetic applications have accumulated in recent years. In parallel, mechanistic understanding has broadened considerably.
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XI References
Rubin, M. B.: Top. Curr. Chem. 13, 251 (1969)
Monroe, B. M.: Adv. in Photochem. 8, 77 (1971)
Rubin, M. B.: in: Excited States in Organic Chemistry and Biochemistry, ed. Pullman, B., Goldblum, N., Reidel, D.: Dordrecht, Holland 1977, p. 381
Swenson, J. R., Hoffmann, R.: Helv. Chim. Acta 53, 2331 (1970)
Cowan, D. O. et al.: Angew. Chem. Int. Ed. Engl. 10, 401 (1971)
Dougherty, D., Brint, P., McGlynn, S. P.: J. Am. Chem. Soc. 100, 5597 (1978)
Arnett, J. F. et al.: ibid. 96, 4385 (1974)
Schang, P. S., Gleiter, R., Rieker, A.: Ber. Bunsenges. Phys. Chem. 82, 629 (1978)
Verheijdt, P. L.: Ph. D. Thesis, University of Amsterdam 1981. A copy of this thesis was kindly provided by Prof. H. Cerfontain
Verheijdt, P. L., Cerfontain, H.: J. Chem. Soc. Perkin II, 1343 (1983)
Sarphatic, L. A., Verheijdt, P. L., Cerfontain, H.: Rec. Trav. Chim. Pays-Bas 102, 9 (1983)
Gleiter, R., Schang, P., Seitz, G.: Chem. Phys. Lett. 55, 144 (1978)
Gleiter, R. et al.: Angew. Chem. Int. Ed. Engl. 16, 400 (1977)
Dougherty, D., Blankespoor, R. L., McGlynn, S. P.: J. Electron. Spectrosc. Relat. Phenom. 16, 245 (1979)
Martin, H.-D. et al.: Chem. Ber. 111, 2557 (1978)
Leonard, N. J., Mader, P. M.: J. Am. Chem. Soc. 72, 5388 (1950)
Mori, T., Nakahari, T., Nozaki, H.: Can. J. Chem. 47, 3266 (1979)
Rubin, M. B., Welner, S.: J. Org. Chem. 45, 1847 (1980)
Rubin, M. B., Migdal, S.: unpublished results
Bloomfield, J. J., Moser, R. E.: J. Am. Chem. Soc. 90, 5625 (1968)
Neely, S. C. et al.: ibid. 93, 4903 (1971)
Bartetzko, R. et al.: ibid. 100, 5589 (1978)
Dougherty, D. et al.: J. Phys. Chem. 80, 2212 (1976)
Gleiter, R., Leismann, H.: University of Heidelberg, to be published
Martin, H.-D., Albert, B., Schiwek, H.-J.: Tetrahedron Lett., 2347 (1979); Israel J. Chem, in press
Weiner, M.: D. Sc. Thesis, Technion 1977
Legon, A. C.: J.C.S. Chem. Comm., 612 (1973); J.C.S. Faraday Trans. II, 651 (1979)
Hagen, K., Hedberg, K.: J. Am. Chem. Soc. 103, 5360 (1981)
Getz, D. et al.: J. Phys. Chem. 84, 768 (1980); Speiser, S. et al.: Chem. Phys. Lett. 61, 199 (1979)
Hassoon, S. et al.: ibid. 98, 345 (1983)
Speiser, S., Katriel, J.: ibid. 102, 88 (1983)
Weinreb, A., Werner, A., Lebovitz, Z.: Photochem. and Photobiol. 29, 755 (1979)
Bera, S. C., Mukherjee, R., Chowdhury, M.: J. Chem. Phys. 51, 754 (1969)
Kaftory, M., Rubin, M. B.' J.C.S. Perkin Trans. II, 149 (1983)
Morantz, D. J., Wright, A. J. C.: J. Chem. Phys. 54, 692 (1971)
Sandross, K.: Acta Chem. Scand. 27, 3021 (1973)
Bera, S. C., Karmakar, B., Chowdhury, M.: Chem. Phys. Lett. 27, 397 (1974)
Arnett, J. F., McGlynn, S. P.: J. Phys. Chem. 79, 626 (1975)
Fang, T.-S., Brown, R. E., Singer, L. A.: J.C.S. Chem. Comm. 116 (1978)
Inoue, H., Sakurai, T.: J.C.S. Chem. Comm., 314 (1983)
Flamigni, L. et al.: J. Photochem. 21, 237 (1983)
Sarphatie, L. A., Verheijdt, P. L., Cerfontain, H.: Recl. Trav. Chim. Pays-Bas 102, 9 (1983)
Charney, E., Tsai, L.: J. Am. Chem. Soc. 93, 7123 (1971)
For leading references see Russell, G. A. et al.: J. Org. Chem. 44, 2780 (1979); Russell, G. A., Schmitt, K. D., Mattox, J.: J. Am. Chem. Soc. 97, 1882 (1975)
Staudinger, H., Anthes, E.: Ber. 46, 1426 (1913)
Haddon, R. C., Poppinger, D., Radom, L.: J. Am. Chem. Soc. 97, 1645 (1975) and references therein
Raine, G. P., Schaefer III, H. F., Haddon, R. C.: J. Am. Chem. Soc. 105, 194 (1983)
Strating, J. et al.: Tetrahedron Lett., 125 (1969)
Chapman, O. L., McIntosh, C. L., Barber, L. L.: J.C.S. Chem. Comm., 1162 (1971)
Obata, N., Takizawa, T.: ibid. 587 (1971)
Toda, F., Todo, E.: Bull. Chem. Soc. Japan 48, 583 (1975)
Dehmlow, E. V.: Tetrahedron Lett., 1271 (1972)
Jung, M. E., Lowe, J. A.: J. Org. Chem. 42, 2371 (1977)
Staab, H. A., Ipaktschi, J.: Chem. Ber. 101, 1457 (1968)
Kolc, J.: Tetrahedron Lett., 5321 (1972)
Chapman, O. L.: Pure and Applied Chem. 40, 511 (1974)
Eggerding, D., West, R.: J. Am. Chem. Soc. 97, 207 (1975); 98, 3641 (1976)
Schmidt, A. H.: Synthesis 961 (1980)
Maier, G., Jung, W. A.: Tetrahedron Lett. 3875 (1980)
Toda, F. et al.: Bull. Chem. Soc. Japan 46, 1737 (1973)
Bloomfield, J. J., Owsley, D. C., Nelke, J. M.: in: Organic Reactions (ed. Dauben, W. G.), Wiley, N.Y. 1976, Vol. 23, Chap. 2
Scharf, H.-D.: Angew. Chem. Int. Ed. Engl. 13, 520 (1974)
Conia, J. M., Robson, M. J.: ibid. 14, 473 (1975)
Rubin, M. B.: unpublished results
Ron, A.: Technion, unpublished results
Verheijdt, P. L., Cerfontain, H.: Recl. Trav. Chim. Pays-Bas 102, 173 (1983)
Bloomfield, J. J., Irelan, J. R. S., Marchand, A. P.: Tetrahedron Lett. 5647 (1968)
Rubin, M. B.: Chimia 35, 406 (1981)
Rubin, M. B., Harel, Y.: unpublished
Liao, C. C. et al.: National Tsing Hua University, unpublished results. We thank Professor Liao for communicating these results prior to publication
Rubin, M. B.: J. Am. Chem. Soc. 103, 7791 (1981)
Heine, H.-G.: Chem. Ber. 104, 2869 (1971)
Denis, J. M., Conia, J. M.: Tetrahedron Lett. 461 (1973)
de Groot, Ae., Oudman, D., Wynberg, H.: ibid. 1529 (1969)
Rubin, M. B., Weiner, M., Scharf, H.-D.: J. Am. Chem. Soc. 98, 5699 (1976)
For reviews of the photochemistry of β,γ-unsataurated ketones see Hixon, S., Mariano, P. S., Zimmerman, H. E.: Chem. Rev. 73, 531 (1973); Dauben, W. G., Lodder, G., Ipaktschi, J.: Top. Curr. Chem, 54, 73 (1975); Houk, K. N.: Chem. Rev. 76, 1 (1976); Schaffner, K.: Tetrahedron 32, 641 (1976)
Rubin, M. B. et al.: J. Photochem. 11, 287 (1979)
Speiser, S., Rubin, M. B., Hassoon, S.: J. Photochem., 26, 297 (1984)
Scharf, H. D., Fleischhauer, J.: Houben Weyl “Metoden der Organischen Chemie” (ed. Muller, E.), Thieme, Stuttgart 1975, Vol. IV 5a, p. 24ff.
Warrener, R. N., Russell, R. A., Lee, T. S.: Tetrahedron Lett., 49 (1977); Warrener, R. N., Pitt, I. G., Russell, R. A.: J.C.S. Chem. Comm., 1136 (1982)
Warrener, R. N., Harrison, P. A., Russell, R. A.: Tetrahedron Lett., 2031 (1977); idem. J.C.S. Chem. Comm. 1134 (1982); Warrener, R. N. et al.: ibid. 546 (1984)
Gream, G. E., Paice, J. C., Ramsay, C. C. R.: Aust. J. Chem. 20, 1671 (1967)
Liao, C. C. et al.: J. Am. Chem. Soc. 104, 292 (1982)
Kunze, M.: Ph. D. Thesis, Univ. Würzburg 1980. We thank Prof. H.-D. Martin for making a part of this thesis available
Paquette, L. A. et al.: J. Am. Chem. Soc. 103, 2262 (1981)
Paquette, L. A. et al.: J. Org. Chem. 48, 1262 (1983)
Scharf, H.-D., Klar, R.: Chem. Ber. 105, 575 (1972)
Bryce-Smith, D., Gilbert, A.: J.C.S. Chem. Comm. 1702 (1968)
Sakanishi, K., Shigeshima, T., Hachiya, H.: Suzuka Kogyo Koto Semmon Gakko Kivo 8, 269 (1975); Chem. Abstr. 88, 74103z (1978)
Verboom, W., Bos, H. J. T.: Recl. Trav. Chim. Pays-Bas 100, 207 (1981)
Pyle, J. L., Schaffer, A. A., Cantrell, J. S.: J. Org. Chem. 46, 115 (1981)
Hart, H., Dean, D. L., Buchanan, D. N.: J. Am. Chem. Soc. 95, 6294 (1973); Vaughan, W. R., Yoshimine, M.: J. Org. Chem. 22, 528 (1957)
Horner, L., Merz, H.: Justus Liebigs Ann. Chem. 570, 7 (1950)
Berney, D., Deslongchamps, P.: Canad. J. Chem. 47, 515 (1969); Pure and Appl. Chem. 49, 1329 (1977)
Chang, T. H. et al.: J. Chinese Chem. Soc. 27, 97 (1980)
Scharf, H.-D., Friedrich, P., Linckens, A.: Synthesis, 256 (1976)
Nunn, E. E., Wilson, W. S., Warrener, R. N.: Tetrahedron Lett., 175 (1972)
Vogel, E., Ippen, J., Buch, V.: Angew. Chem. Int. Ed. Engl. 14, 566 (1975)
Warrener, R. N., Nunn, E. E., Paddon-Row, M. N.: Tetrahedron Lett., 2355 (1976)
Friedrichsen, W., Schroer, W.-D., Schmidt, R.: Ann., 793 (1976); Tetrahedron Lett., 2469 (1974); Allmann, R. et al.: Tetrahedron 32, 147 (1976)
Friedrichsen, W. et al.: Justus Liebigs Ann. Chem., 440 (1978)
Christl, M. et al.: Chem. Ber. 110, 3745 (1977)
Pritschins, W., Grimme, W.: Tetrahedron Lett., 4545 (1979)
Grimme, W. et al.: Angew. Chem. Int. Ed. Engl., 20, 113 (1981); cf. also Chem. Ber. 114, 3197 (1981)
Shimizu, N., Bartlett, P. D.: J. Am. Chem. Soc. 98, 4193 (1976)
Bartlett, P. O., Roof, A. A. M., Shimizu, N.: ibid. 104, 3130 (1982)
Mori, A., Takeshita, H.: Chem. Lett., 395 (1978)
Koo, J.-Y., Schuster, G. B.: J. Org. Chem. 44, 847 (1979)
Buchi, G., Fowler, K. W., Nadzan, A. M.: J. Am. Chem. Soc. 104, 544 (1982)
Bartlett, P. D., Becherer, J.: Tetrahedron Lett., 2983 (1978)
Turro, N. J., Lee, J.-J.: J. Am. Chem. Soc. 91, 5651 (1969)
Zepp, R. G., Wagner, P. J.: ibid. 92, 7466 (1970)
Wagner, P. J. et al.: ibid. 98, 8125 (1976)
Hamer, N. K.: J.C.S. Perkin Trans. I, 61 (1983)
Burkoth, T. L., Ullman, E. F.: Tetrahedron Lett., 145 (1970)
Bishop, R.: J.C.S. Chem. Comm., 1288 (1972)
Urry, W. H., Duggan, J. C., Pai, M. H.: J. Am. Chem. Soc. 92, 5785 (1970)
Urry, W. H., Trecker, D.: ibid. 84, 118 (1962)
Paquette, L. A., Balogh, D. W.: ibid. 104, 74 (1982)
Balogh, D. W. et al.: ibid. 103, 226 (1981)
Nerbonne, J. M., Weiss, R. C.: Israel J. Chem. 18, 266 (1979)
Kelder, K., Cerfontain, H., van der Wielen, F. W. M.: J.C.S. Perkin Trans. II, 710 (1970)
Turro, N. J., Lee, T. J.: J. Am. Chem. Soc. 92, 7467 (1970)
Bishop, R., Hamer, N. K.: J. Chem. Soc. (C), 1197 (1970); idem, J.C.S. Chem. Comm., 804 (1969)
Ogata, Y., Tagaki, K.: Bull. Chem. Soc. Japan 47, 2255 (1974)
Rigaudy, J., Paillous, N.: Bull. Soc. Chim. France, 576 (1971)
Bishop, R., Hamer, N. K.: J. Chem. Soc. (C), 1193 (1970)
Ogata, Y., Tagaki, K.: J. Org. Chem. 39, 1385 (1974)
Bishop, R., Hamer, N. K.: JCS Chem. Comm., 804 (1969)
Hamer, N. K., Samuel, C. J.: J.C.S. Perkin Trans. II, 1316 (1973)
Hamer, N. K.: J.C.S. Perkin Trans. I, 508 (1979)
Ogata, Y., Tagaki, K., Fuji, Y.: J. Org. Chem. 37, 4026 (1972)
Paukstelis, J. V., Kao, J.-L.: Tetrahedron Lett., 3691 (1970)
Maruyama, K., Ono, K., Osugi, J.: Bull. Chem. Soc. Japan 45, 847 (1972)
Ryang, H.-S., Shima, K., Sakurai, H.: J. Am. Chem. Soc. 93, 5270 (1971); J. Org. Chem. 38, 2860 (1973)
Turro, N. J. et al.: Tetrahedron Lett. 21, 2775 (1980)
Chow, Y. L. et al.: Can. J. Chem. 48, 3045 (1970)
Sauers, R. R., Valenti, P. C., Tavss, E.: Tetrahedron Lett., 3129 (1975)
Sauers, R. R., Valenti, P. C., Crichlow, C. A.: J. Am. Chem. Soc. 104, 6378 (1982)
Jones, G., II, Santhanam, M., Chiang, S.-H.: ibid. 102, 6088 (1980)
Shima, K. et al.: Bull. Chem. Soc. Japan 50, 761 (1977)
Rubin, M. B., Ben-Bassat, J. M., Weiner, M.: Israel J. Chem. 16, 326 (1977)
Gream, G. E., Mular, M., Paice, J. C.: Tetrahedron Lett., 3479 (1970)
Mosterd, A., Matser, H., Bos, H. J. T.: ibid. 4179 (1974)
Turro, N. J., Engel, R.: J. Am. Chem. Soc. 91, 7113 (1969)
Greame, G. E., Paice, J. C., Uszynski, B. S. J.: J.C.S. Chem. Comm. 895 (1970)
McLauchlan, K. A., Sealy, R. C., Wittmann, J. M.: J.C.S. Perkin Trans. II, 926 (1977); Mol. Physics 36, 1397 (1978)
Mehrotra, K. N., Pandey, G. P.: Bull. Chem. Soc. Japan 53, 1081 (1980)
Scaiano, J. C.: J. Phys. Chem. 85, 2851 (1981)
Rubin, M. B., Neuwirth-Weiss, Z.: J. Am. Chem. Soc. 94, 6048 (1972)
Kooi, J., Wynberg, H., Kellogg, R. M.: Tetrahedron 29, 2135 (1973)
Rubin, M. B., Inbar, S.: J. Am. Chem. Soc. 100, 2266 (1978)
Rubin, M. B., Hershtik, Z.: J.C.S. Chem. Comm., 1267 (1970)
Engel, P. S., Monroe, B. M.: Adv. Photochem. 8, 245 (1971)
Rubin, M. B.: Tetrahedron Lett., 3931 (1969)
Gutmann, A. L.: M.Sc. Thesis, Technion 1978
Johnson, P. Y., Zitsman, J., Hatch, C.: J. Org. Chem. 38, 4087 (1973); Tetrahedron Lett., 1991 (1972)
Greame, G. E., Paice, J. C.: Aust. J. Chem. 22, 1249 (1969)
Hirano, H., Kurumaya, K., Tada, M.: Bull. Chem. Soc. Japan 54, 2708 (1981)
Boyer, J. H., Srinivasan, K. G.: J.C.S. Chem. Comm., 699 (1973)
Tabushi, I., Kojo, S., Fukunishi, K.: J. Org. Chem. 43, 2370 (1978)
Bunbury, D. L., Chan, T. M.: Can. J. Chem. 50, 2499 (1972)
Steinberg, N., Gafni, A., Steinberg, I. Z.: J. Am. Chem. Soc. 103, 1636 (1981)
Broomhead, E. J., McLauchlan, K. A., Roe, J. C.: J.C.S. Perkin Trans II, 796 (1980) and references therein
Monroe, B. M., Lee, C., Turro, N. J.: Mol. Photochem. 6, 271 (1974)
Schuh, M. D.: J. Phys. Chem. 82, 1861 (1978)
Shepherd, J. P.: J. Org. Chem. 48, 337 (1983)
Clennan, E. L., Speth, D. R., Bartlett, P. D. ibid. 48, 1246 (1983)
Mattay, J. et al.: J. Photochem., 23, 319 (1983)
Mattay, J. et al.: Angew. Chem. Int. Ed. Engl., 23, 249 (1984); Tetrahedron Lett., 25, 817 (1984); Proceedings Xth IUPAC Symposium on Photochemistry, Interlaken, 1984, p. 227
Hassoon, S. et al.: J. Phys. Chem., in press
Rubin, M. B. et al.: Isr. J. Chem., in press
Speiser, S., Hassoon, S., Rubin, M. B., Proc. Xth IUPAC Symposium on Photochemistry, Interlaken, 1984, p. 227
Chan, L. Y., Heath, B. A.: J. Chem. Phys., 171, 1070 (1979)
Pawlikowski, M., Zgierski, M. Z., Orlando, G.: Chem. Phys. Lett., 105, 612 (1984)
Rubin, M. B., Proc. Xth IUPAC Symposium on Photochemistry, Interlaken, 1984, p. 173
Sawaki, Y., Foote, C. S.: J. Org. Chem., 48, 4934 (1983)
Sawaki, Y.: Bull. Chem. Soc. Japan, 56, 3464 (1983)
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Rubin, M.B. (1985). Recent photochemistry of α-diketones. In: Photochemistry and Organic Synthesis. Topics in Current Chemistry, vol 129. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-15141-9_1
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