Photochemical synthesis of novel 4,5,9,10-tetraaryl-tricyclo[6.2.0.03,6]decane-2,7-diones: a theoretical view of photodimerization

详细信息    查看全文

• 作者：Johnson George ; Jaimala Sharma ; Rahul Joshi…
• 关键词：Chalcones ; Photodimerization ; Diradical mechanism ; DFT calculations
• 刊名：Research on Chemical Intermediates
• 出版年：2015
• 出版时间：August 2015
• 年：2015
• 卷：41
• 期：8
• 页码：5681-5689
• 全文大小：537 KB
• 参考文献：1.N. Yayli, O. Ucuncu, A. Yasar, Y. Gok, M. Kucuk, S. Kolayli, Turk. J. Chem. 515, 25 (2004)
  2.H. Wunscher, G. Haucke, P. Czerney, U. Kurzer, J. Photochem. Photobiol. A 75, 151 (2002)
  3.J. Anthony, M.A. Thomson, M.S. Patrick, L.E. John, H. Ian, G. Keira, L.M. James, H.L. Annette, B. John, Chem. Abstr. 137, 47052f (2002)
  4.N. Yayli, O. Ucuncu, A. Yasar, Y. Gok, M. Kucuk, S.A. Karaoglu, J. Photochem. Photobiol. A. (2006)
  5.E. Saguin, E. Elomori, P. Magiatis, A.L. Skaltsounis, L.R. Chao, F. Tillequin, Nat. Prod. Lett. 187, 16 (2002)
  6.A.E. Tih, R.G. Tih, B.L. Sondengam, M.T. Martin, B. Bodo, J. Nat. Prod. Downers Grove III; Am. Soc. Pharmacog. 964, 53 (1990)
  7.S.E. Drewes, N.A. Hudson, R.B. Bates, G.S. Linz, J. Chem. Soc. Perkin Trans. 2809, 1 (1987)
  8.D.R. Katerere, A.I. Gray, A.R. Kennedy, R.J. Nash, R.D. Waigh, Phytochemistry 433, 65 (2004)
  9.F.R. Cibin, G. Doddi, P. Mencarelli, Tetrahedron 3455, 59 (2003)
  10.D. Auria, R. Rocco, J. Photochem. Photobiol. A 557, 163 (2004)
  11.N.-X. Wang, Tetrahedron 2377, 58 (2002)
  12.B.I. Kamara, T.L. Manong, E.V. Brandt, Phytochemistry 1126, 66 (2005)
  13.N.I. Rtishchev, G.I. Nosova, N.A. Solovskaya, V.A. Lukyashina, E.F. Galaktionova, V.V. Kudryantsev, Russ. J. Gen. Chem. 1272, 71 (2004)
  14.Y. Kanao, M. Iyoda, M. Oda, Tetrahedron Lett. 1727, 24 (1983)
  15.R.P. Hsuang, C.A. Zificsak, L.L. Wei, C.J. Douglas, H. Xiong, J.A. Mulder, Org. Lett. 1237, 1 (1999)
  16.I. Abraham, R. Joshi, P. Pardasani, R.T. Pardasani, J. Braz. Chem. Soc. 385, 22 (2011)
  17.S. Verma, B. Srivastava, K. Sharma, R. Joshi, P. Pardasani, R.T. Pardasani, Res. Chem. Intermed. 723, 38 (2012)
  18.D.D. Perrin, W.L.F. Armarego, D.R. Perrin, Purification of Laboratory Chemicals, 2nd edn. (Pergamon, Oxford, 1998)
  19.A.I. Vogel, Vogel鈥檚 Text Book of Practical Organic Chemistry, 4th edn. (ELBS Longman, London, 1984)
  20.M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr. T. Vreven, K. N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 98, Revision A.5. (Gaussian, Inc., Pittsburgh, 1998)
  21.P.N. Rao, Indian J. Pharma. Sci. 207, 51 (1989)
  22.K.D. Jordan, Int. J. Quantum Chem. Symp. 7, 491 (1973)View Article
  23.Y.L. Chow, T.C. Joseph, Chem. Commun. 11, 604 (1968)
  24.Y.L. Chow, T.C. Joseph, J. Org. Chem. 41, 2223 (1976)View Article
  
• 作者单位：Johnson George (1)
  Jaimala Sharma (1)
  Rahul Joshi (1)
  Ramchand T. Pardasani (2)
  
  1. Department of Chemistry, University of Rajasthan, Jaipur, 302055, India
  2. Department of Chemistry, Central University of Rajasthan, Bandarsindri, Ajmer, 305801, India
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Catalysis
  Physical Chemistry
  Inorganic Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1568-5675

文摘

A sequence of photodimerization reactions of 1,5-diaryl-1,4-pentadien-3-ones have been carried out to produce 4,5,9,10-tetraaryl-tricyclo[6.2.0.03,6]decane-2,7-diones. The title compounds were characterized by means of infrared (IR), nuclear magnetic resonance (NMR) and mass spectrometric methods. The reaction proceeds via a diradical stepwise mechanism through the triplet excited state with asynchronous ring closure. Density functional theory calculations have been well established to probe the mechanism of photodimerization. The diradical mechanism for dimerization of chalcone proceeds via ring closure of the complex formed by two molecules.