Solid-State Photocycloaddition Reactions of Tri-2-Pyrones with Benzophenone

Wei Dong Wang; Tetsuro Shimo

doi:10.4028/www.scientific.net/AMR.554-556.796

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HomeAdvanced Materials ResearchAdvanced Materials Research Vols. 554-556Solid-State Photocycloaddition Reactions of...

Solid-State Photocycloaddition Reactions of Tri-2-Pyrones with Benzophenone

Abstract:

Solid-state photocycloaddition reactions between tri-2-pyrones (1a,1b) with benzophenone (2) gave the corresponding oxetane derivatives (3a:3a′=1:1 and 3b:3b′=1:1, 1:2 adducts) with high site- and regioselectivity across the C5-C6 , C5′-C6′ and C5′′-C6′′ double bonds in 1 via the triplet excited state of 2. The site- and regioselectivities were explained by MO calculations. The hydrogen-bonding interaction between 2 and 1a, 1b and the triplet reaction mechanism were also explained by the IR analyses and the quenching experiments, respectively.

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Periodical:

Advanced Materials Research (Volumes 554-556)

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796-800

DOI:

https://doi.org/10.4028/www.scientific.net/AMR.554-556.796

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Online since:

July 2012

Authors:

Wei Dong Wang, Tetsuro Shimo

Keywords:

[2+2] Cycloadducts, Benzophenone, Photocycloaddition Reactions, Solid-State, Tri-2-Pyrones

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References

[1] Y. Ito, Synthesis 1998, 1 and references cited therein.

Google Scholar

[2] Y. Ito and H. Fujita, Chem. Lett. (2000), p.288.

Google Scholar

[3] K. Tanaka and F. Toda, Chem. Rev. Vol. 100 (2000), p.1025.

Google Scholar

[4] H. Koshima, H. Kawanishu, M. Nagano, H. Yu, M. Shiro, T. Hosoya, H. Uekusa and Y. Ohashi, J. Org. Chem. Vol. 70 (2005), p.4490.

DOI: 10.1021/jo0500784

Google Scholar

[5] T. Obata, T. Shimo, S. Yoshimoto, K. Somekawa and M. Kawaminami, Chem. Lett. (1999), p.181.

Google Scholar

[6] T. Obata, T. Shimo, M. Yasutake, T. Shinmyozu and K. Somekawa, Tetrahedron Vol. 57 (2001), p.1531.

Google Scholar

[7] T. Shimo, T. Uezono, T. Obata, M. Yasutake, T. Shinmyozu and K. Somekawa, Tetrahedron Vol. 58 (2002), P. 6111.

DOI: 10.1016/s0040-4020(02)00582-3

Google Scholar

[8] T. Shimo and K. Somekawa: Organic Photochimistry and Photobiology (CRC Press, USA 2003).

Google Scholar

[9] T. Shimo, R. Yamaguchi, Y. Odo and K. Somekawa, Heterocycles Vol. 63 (2004), p.1541.

Google Scholar

[10] W. D. Wang, T. Shimo, T. Shinmyozu, T. Iwanaga and K. Somekawa, Heterocycles Vol. 68 (2006), p.1381.

Google Scholar

[11] W. D. Wang, T. Shimo, H. Hashimoto and K. Somekawa, Tetrahedron Vol. 63 (2007), p.12367.

Google Scholar

[12] Y. Ito, M. Ji-Ben, S. Suzuki, Y. Kusunaga and T. Matsuura, Tetrahedron Lett. Vol. 26 (1985), P. 2093.

Google Scholar

[13] T. Kang and J. R. Scheffer, Org. Lett. Vol. 3 (2001), P. 3361.

Google Scholar

[14] Y. Odo, T. Shimo, K. Hori and K. Somekawa, Bull. Chem. Soc., Jpn. Vol. 77 (2004), p.1209.

Google Scholar