Photolysis and cycloaddition reactivity of diferrocenyl substituted cyclopentadienone

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.

Keywords

Cyclopentadienone / Reactivity / Photolysis / Cycloaddition / Crystal structure

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, 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 L., 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.