Photolysis and Cycloaddition Reactivity of Diferrocenyl Substituted Cyclopentadienone

doi:10.1007/s40242-016-6158-7

Abstract

Abstract:

The photolysis results of new diferrocenyl substituted cyclopentadienone(3) show that sunlight and air play an important role in the decomposition of compound 3, and two new compounds, 2-cyclopentenone(4) and α-pyrone(5), were obtained via photolysis of compound 3. The photolysis process was investigated by ¹H NMR, and a plausible mechanism for the formation of compound 5 was deduced. The cycloaddition reactions of substituted cyclopentadienones(3, 7, 9) with maleimide gave substituted imides 8, 10, 11, 12 and an unprecedented diferrocenyl substituted 1H-pyrrol-3(2H)-one derivative 13, respectively. The structures of compounds 4, 5, 8, 10, 11, 12 and 13 were confirmed by X-ray single crystal diffraction analysis technique.

Key words: Cyclopentadienone, Reactivity, Photolysis, Cycloaddition, Crystal structure

ZHANG Xiaoyong, HAN Limin, GAO Yuanyuan, SHI Jiale, SUO Quanling. Photolysis and Cycloaddition Reactivity of Diferrocenyl Substituted Cyclopentadienone[J]. Chemical Research in Chinese Universities, 2016, 32(5): 775-780.

References

[1] Ogliaruso M. A., Romanelli M. G., Becker E. I., Chem. Rev., 1965, 65(3), 261
[2] Zhang X. Y., Han L. M., Zhu N., Gao Y. Y., Suo Q. L., Chem. Res. Chinese Universities, 2015, 31(5), 736
[3] Liebeskind L. S., Bombrum A., J. Am. Chem. Soc., 1991, 113(23), 8736
[4] Mackay D., Papadopoulos D., Taylor N. J., J. Chem. Soc., Chem. Commun., 1992, 4, 325
[5] Knölker H. J., Baum E., Heber J., Tetrahedron Lett., 1995, 36(42), 7647
[6] Rainier J. D., Imbriglio J. E., Org. Lett., 1999, 1(12), 2037
[7] Wiesler U. M., Müllen K., Chem. Commun., 1999, 22, 2293
[8] Luo Q., Wang C., Zhang W. X., Xi Z. F., Chem. Commun., 2008, 13, 1593
[9] Martin C. J., Gil B., Perera S. D., Draper S. M., Chem. Commun., 2011, 47, 3616
[10] Loser P., Winzenburg A., Faust R., Chem. Commun., 2013, 49, 9413
[11] Wijesinghe L. P., Lankage B. S., Maille G. M. O., Perera S. D., Nolan D., Wang L. S., Draper S. M., Chem. Commun., 2013, 50, 10637
[12] Gleiter R., Werz D. B., Organometallics, 2005, 24(18), 4316
[13] Casey C. P., Bikzhanova G. A., Guzei I. A., J. Am. Chem. Soc., 2006, 128(7), 2286
[14] Thorson M. K., Klinkel K. L., Wang J., Williams T., Eur. J. Inorg. Chem., 2009, 2009(2), 295
[15] Slugovc C., Mauthner K., Mereiter K., Schmid R., Kirchner K., Organometallics, 1996, 15, 2954
[16] Haak E., Eur. J. Org. Chem., 2007, 2007(17), 2815
[17] Godschalx J. P., Romer D. R., So Y. H., Lysenko Z., Mills M. E., Buske G. R., Townsend P. H., Smith. D. W., Martin S. J., Devries R. A., Polyphenylene Oligomers and Polymers, US 5965679, 1997
[18] Maier G., Pfriem S., Schafer U., Matusch R., Angew. Chem., 1978, 90(7), 552
[19] Maier G., Pfriem S., Schafer U., Malsch K. D., Matusch R., Chem. Ber., 1981, 114(12), 3965
[20] Tanaka K., Taniguchi T., Ogasawara K., Tetrahedron Lett., 2001, 42(6), 1049
[21] Walters R. S., Kraml C. M., Byrne N., Ho D. M., Qin Q., Coughlin F. J., Bernhard S., Pascal R. A. Jr., J. Am. Chem. Soc., 2008, 130(48), 16435
[22] Neudorff W. D., Schulte N., Lentz D., Schlulter A. D., Org. Lett., 2001, 3(20), 115
[23] Smyth N., Engen D. V., Pascal R. A. Jr., J. Org. Chem., 1990, 55(6), 1937
[24] Szulczyk D., Bielenica A., Dobrowolski M. A., Dobrzycki ?., Krawiecka M., Kuran B., Struga M., Med. Chem. Res., 2014, 23(3), 1519
[25] McAdam C. J., Brunton J. J., Robinson B. H., Simpson J., J. Chem. Soc. Dalton Trans., 1999, 2487
[26] Dennis G. D., Davis D. E., Field L. D., Masters A. F., Maschmeyer T., Ward A. J., Buys I. E., Turner P., Aust. J. Chem., 2006, 59(2), 135
[27] McGlacken G. P., Fairlamb I. J. S., Nat. Prod. Rep., 2005, 22, 369
[28] Fairlamb I. J. S., Marrison L. R., Dickinson J. M., Lu F. J., Schmidta J. P., Bioorg. Med. Chem., 2004, 12(15), 4285
[29] Wu P. L., Hsu Y. L., Wu T. S., Bastow K. F., Lee K. H., Org. Lett., 2006, 8(22), 5207
[30] Hagiwara H., Kobayashi K., Miya S., Hoshi T., Suzuki T., Ando M., Org. Lett., 2001, 3(2), 251
[31] Puerta D. T., Mongan J., Tran B. L., McCammon J. A., Cohen S. M., J. Am. Chem. Soc., 2005, 127(41), 14148
[32] Thaisrivongs S., Janakiraman M. N., Chong K. T., Tomich P. K., Dolak L. A., Turner S. R., Strohbach J. W., Lynn J. C., Horng M. M., Hinshaw R. R., Watenpaugh K. D., J. Med. Chem., 1996, 39(12), 2400
[33] Appendino G., Ottino M., Marquez N., Bianchi F., Giana A., Ballero M., Sterner O., Fiebich B. L., Munoz E., J. Nat. Prod., 2007, 70(4), 608
[34] Rosenblum M., Brawn N., King B., Tetrahedron Lett., 1967, 8(45), 4421
[35] Harrington L. E., Britten J. F., McGlinchey M. J., Canadian Journal of Chemistry, 2003, 81(11), 1180
[36] Mueller-Westerhoff U. T., Zhou M., J. Org. Chem., 1994, 59(17), 4988
[37] Xu H. Y., Zhang X. Y., He Y., Guo S. H., Fan X. S., Chem. Commun., 2012, 48, 3121
[38] Mochida S., Hirano K., Satoh T., Miura M., J. Org. Chem., 2009, 74(16), 6295
[39] Kuninobu Y., Kawata A., Nishi M., Takata H., Takai K., Chem. Commun., 2008, 47, 6360
[40] Kajita Y., Kurahashi T., Matsubara S., J. Am. Chem. Soc., 2008, 130(51), 17226
[41] Lee W. B., Kwak K. T., Journal of the Korean Chemical Society, 1995, 39(2), 136
[42] Takata T., Tajima R., Ando W., Chemistry Letters, 1985, 14(5), 665
[43] Padwa A., Hartman R., J. Am. Chem. Soc., 1966, 88(7), 1518
[44] Ishibe N., Sunami M., Odani M., J. Am. Chem. Soc., 1973, 95(2), 463
[45] Gupta H. K., Stradiotto M., Hughes D. W., McGlinchey M. J., J. Org. Chem., 2000, 65(2), 3652
[46] Smyth N., Engen D. V., Pascal R. A., J. Org. Chem., 1990, 55(6), 1937
[47] Qiao X. X., Padula M. A., Ho D. M., Vogelaar N. J., Schutt C. E., Pascal R. A., J. Am. Chem. Soc. 1996, 118(4), 741
[48] Li P. H., Zhang X. L., Wang L., Organic. Lett., 2014, 16(8), 2126
[49] Smith A. B., Hirschmann R., Pasternak A., Guzman M. C., Yokoyama A., Sprengeler P. A., Darke P. L., Emini E. A., Schlei P. W. A., J. Am. Chem. Soc., 1995, 117(45), 11113
[50] Smith A. B., Hirschmann R., Pasternak A., Yao W. Q., Sprengeler P. A., J. Med. Chem., 1997, 40(16), 2440
[51] Smith A. B., Charnley A. K., Hirschmann R., Accounts of Chemical Research, 2011, 44(3), 180
[52] Smith A. B., Cantin L. D., Pasternak A., Zawacki L. G., Yao W. Q., Charnley A. K., Barbosa J., Sprengeler P. A., Hirschmann R., Munshi S., Olsen D. B., Schleif W. A., Kuo L. C., J. Med. Chem., 2003, 46(8), 1831
[53] Vanel R., Berthiol F., Bessières B., Einhorn C., Einhorn J., Synlett., 2011, 2011(9), 1293