Diastereoselective [2+2] Photocycloaddition of a Chiral Cyclohexenone with Ethylene in a Continuous Flow Microcapillary Reactor
Tóm tắt
The diastereoselective [2+2] photocycloaddition of ethylene to a chiral cyclohexenone was studied in a continuous flow microcapillary reactor. In all cases examined, the microcapillary reactor gave higher conversions and selectivity than the batch system, even after shorter irradiation times. These findings were explained by the superior temperature control, favorable light penetration, and generation of a gas-liquid slug flow with improved mass transfer in the microreactor.
Tài liệu tham khảo
Ciana, C.-L.; Bochet, C. G. Chimia 2007, 61, 650.
Oelgemöller, M.; Healy, N.; de Oliveira, L.; Jung, C.; Mattay, J. Green Chem. 2006, 8, 831.
Hoffmann, N. Chem. Rev. 2008, 108, 1052.
Bach, T.; Hehn, J. P. Angew. Chem. Int. Ed. 2011, 50, 1000.
Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449.
Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873.
Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485.
Shimada, Y.; Nakamura, M.; Suzuka, T.; Matsui, J.; Tatsumi, R.; Tsutsumi, K.; Morimoto, T.; Kurosawa, H.; Kakiuchi, K. Tetrahedron Lett. 2003, 44, 1301.
Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003.
Crimmins, M. T. Chem. Rev. 1988, 88, 1453.s
Oelgemöller, M. Chem. Eng. Technol. 2012, 35, DOI: 10.1002/ceat.201200009.
Oelgemöller, M.; Shvydkiv, O. Molecules 2011, 16, 7522.
Coyle, E. E.; Oelgemöller, M. Photochem. Photobiol. Sci. 2008, 7, 1313.
Fukuyama, T.; Kajihara, Y.; Hino, Y.; Ryu, I. J. Flow Chem. 2011, 1, 40.
Shvydkiv, O.; Yavorskyy, A.; Tan, S. B.; Nolan, K.; Hoffmann, N.; Youssef, A.; Oelgemöller, M. Photochem. Photobiol. Sci. 2011, 10, 1399.
Sakeda, K.; Wakabayashi, K.; Matsushita, Y.; Ichimura, T.; Suzuki, T.; Wada, T.; Inoue, Y. J. Photochem. Photobiol. A: Chem. 2007, 192, 166.
Maeda, H.; Mukae, H.; Mizuno, K. Chem. Lett. 2005, 34, 66.
Tsutsumi, K.; Yanagisawa, Y.; Furutani, A.; Morimoto, T.; Kakiuchi, K.; Wada, T.; Mori, T.; Inoue, Y. Chem. Eur. J. 2010, 16, 7448.
Tsutsumi, K.; Terao, K.; Yamaguchi, H.; Yoshimura, S.; Morimoto, T.; Kakiuchi, K.; Fukuyama, T.; Ryu, I. Chem. Lett. 2010, 39 (8), 828.
Horie, T.; Sumino, M.; Tanaka, T.; Matsushita, Y.; Ichimura, T.; Yoshida, J. I. Org. Proc. Res. Devel. 2010, 14, 405.
Gutierrez, A. C.; Jamison, T. F. Org. Lett. 2011, 13, 6414.
Yavorskyy, A.; Shvydkiv, O.; Nolan, K.; Hoffmann, N.; Oelgemöller, M. Tetrahedron Lett. 2010, 52, 278.
Hook, B. D. A.; Dohle, W.; Hirst, P. R.; Pickworth, M.; Berry, M. B.; Booker-Milburn, K. I. J. Org. Chem. 2005, 70, 7558.
Lévesque, F.; Seeberger, P. H. Angew. Chem. Int. Ed. 2012, 51, 1706.
Chen, L.; Tia, Y. S.; Karayiannis, T. G. Int. J. Heat Mass Transfer 2006, 49, 4220.
Yavorskyy, A.; Shvydkiv, O.; Limburg, C.; Nolan, K.; Delauré, Y. M. C.; Oelgemöller, M. Green Chem. 2012, 14, 888.
Liang-sun, L.; Ruey-fu, S.; Hsin-jung, O.; Tien-san, L. Ind. Eng. Chem. Res. 2003, 42, 6977.
Rupak, K.; Sudhakar, P.; Krishna, R. S.; Viral, P.; Shashikant, S.; Parimal, A. P. J. Appl. Poly. Sci. 2011, 122, 2646.
Sugimoto, A.; Fukuyama, T.; Sumino, Y.; Takagi, M.; Ryu, I. Tetrahedron 2009, 65, 1593.
Vasudevan, A.; Villamil, C.; Trumbull, J.; Olson, J.; Sutherland, D.; Pan, J.; Djuric, S. Tetrahedron Lett. 2010, 51, 4007.
Nettekoven, M.; Püllmann, B.; Martin, R. E.; Wechsler, D. Tetrahedron Lett. 2012, 53, 1363.