Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Photocyclization of 1,2-Bispyrazylethylene and 2-Styrylpyrazine

  • Published : 1980.06.30
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Abstract

1,4,5,8-Tetraazaphenanthrene, a new tetraazaheteroaromatic compound, has been synthesized photochemically in 90 % yield and quantum yield of $5.1{\times}10^{-2}$ from dilute benzene solutions of 1,2-bispyrazyl ethylene(BPE) in the presence of oxygen as an oxidant. Iodine was not appropriate oxidant because of strong complexing with BPE and also enhanced intersystem crossing of BPE and thereby decreasing the photocyclization of BPE. Salt effect, solvent effect, and quenching and sensitization studies on the photocyclization of BPE have shown that ($^l(n, {\pi}^*$) is the reactive state for the cyclization in comparison to ($^1{\pi}, {\pi}^*$) state for the ordinary stilbene derivatives.

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References

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  1. Photocyclization reaction of 5-styryl-1,3-dimethyl-uracil vol.32, pp.3, 1980, https://doi.org/10.1016/0047-2670(86)87084-8