Polyethylene Beads에 결합시킨 광증감제 α-Diketone의 합성과 1,3-Dimethylethymine의 광산화반응

윤종엽; 용대운; 장순재; 한보섭

Polymer(Korea), Vol.17, No.6, 622-629, November, 1993

Synthesis of α-Diketone Sensitizer Bound on the Polystyrene Beads and Photooxidation of 1,3-Dimethylthymine

Polystyrene beads bound α-diketones, 4-(1,2-dioxo-2-phenylethyl)polystyren and 4-(1,2-dioxopropyl) polystyrene were synthesized. Photolysis of oxygen saturated solution of 1,3-dimethylthymine in the presence of the insoluble polymer bound α-diketone and subsequent treatment of the unstable intermediate with nucleophiles produced sterco- and regio-specific 5-hydroxy-6-substituted dihydro-1,3-dimethylthymine derivatives. High recovery of polymer-bound benzil after photooxygenation showed it was significantly more stable toward bleaching than the free α-diketones and could be reused at least five times.

[References]

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[1] Bezman SA, Burtis PA, J. Photochem. Photobiol., 28, 325 (1978)

[2] Gollnick K, Resear., 328 (1974)

[3] Foote CS, "Free Radicals in Biology," Vol. Ed., Acad. Press, N.Y.N.Y. (1976)

[4] Nonxon JA, Can. J. Phys., 39, 1110 (1961)

[5] Jones ITN, Wayne RP, J. Chem. Phys., 51, 3617 (1969)

[6] Khan AU, Kasha M, J. Chem. Phys., 39, 2105 (1963)

[7] Khan AU, Kasha M, J. Chem. Phys., 40, 605 (1964)

[8] Foote CS, Wexler S, J. Am. Chem. Soc., 86, 3879 (1964)

[9] Murray RW, Kaplan ML, J. Am. Chem. Soc., 90, 537 (1968)

[10] Wasserman WH, Schaeffer JR, J. Am. Chem. Soc., 89, 3073 (1967)

[11] Peters JW, Pitts JN, Rosenthal I, Fuhr H, J. Am. Chem. Soc., 94, 4348 (1972)

[12] Chambers RW, Kearns DS, J. Photochem. Photobiol., 10, 215 (1969)

[13] Shimizu NS, Bartlett PD, J. Am. Chem. Soc., 98, 4193 (1976)

[14] Gollnick K, Franken T, Schade G, Dorhofer G, Ann. N.Y. Acad. Sci., 171, 89 (1963)

[15] Schenck GO, Becker HD, Schulte-Elte KH, Kranch CH, Chem. Ber., 96, 509 (1963)

[16] Ho TL, Synthesis, 697 (1972)

[17] Lieto J, Milstein D, Albright RL, Minkiewicz JV, Gates BC, Chemtech., 46 (1983)

[18] Ottenheum HCJ, deMan JHM, Synthesis, 163 (1975)

[19] Frechet JMJ, Hazue KE, Macromolecules, 8, 130 (1975)

[20] Farral MJ, Frechet JMJ, J. Org. Chem., 41, 3877 (1976)

[21] Ryang HS, Wang SY, J. Am. Chem. Soc., 100, 1302 (1978)

[22] Hahn BS, Wang SY, Biochem. Biophys. Reses. Commu., 77, 947 (1977)

[23] Ryang HS, Wang SY, J. Org. Chem., 44, 1191 (1979)

[24] Jefford CW, Boschung AF, Helv. Chim. Acta, 60, 2673 (1977)

[25] Bartlett PD, Ho MS, J. Am. Chem. Soc., 96, 627 (1974)

[26] Partlett PD, Chem. Soc. Rev., 5, 154 (1976)

[27] Galluci RR, J. Org. Chem., 48, 342 (1983)

[28] Saltiel J, Curtis HC, Moi. Photochem., 1, 239 (1969)

[29] Wadt WR, Goddard WA, J. Am. Chem. Soc., 97, 3004 (1976)

[30] Bartlett PD, Landis ME, J. Am. Chem. Soc., 99, 3033 (1977)

[31] Bartlett PD, Becherer J, Tetrahedron Lett., 33, 2983 (1978)

[32] Hahn BS, Wang SY, J. Am. Chem. Soc., 94, 4764 (1972)

[33] Battistini C, Balsamo A, Berti G, Crotti P, Macchia B,Macchia F, J. Chem. Commun., 712 (1974)

[34] Eliel EL, Accounts Chem. Res., 3, 1 (1970)

[35] Robins MJ, MacCoss M, Naikand SR, Ramani G, J. Am. Chem. Soc., 98, 7381 (1976)

[36] Clark-Lewis JW, Thompson MJ, J. Chem. Soc., 2401 (1959)