Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Photoreaction of 1,4-Disubstituted-1,3-Butadiyne with Alcohol

  • Lee, Tae-Suk (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Shim, Sang-Chul (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Kim, Sung-Sik (Department of Chemistry, Chonbuk National University)
  • Published : 1986.04.20
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Abstract

Irradiation of 1,4-diphenyl-1,3-butadiyne and 5,5-dimethyl-1-phenyl-1,3-hexadiyne with methanol yields 1:1 polar addition products, [E]- and [Z]-1,4-diphenyl-1-methoxy-1-buten-3-yne and [E]- and [Z]-5,5-dimethyl-1-methoxy-1-phenyl-1-hexen-3-yne, respectively. These geometrical isomers were converted into each other reaching the photostationary state on irradiation with 300 nm UV light. The photoaddition reaction of 1,4-diphenyl-1,3-butadiyne and 5,5-dimethyl-1-phenyl-1,3-hexadiyne with methanol seems to proceed from the zwitterionic lowest excited state.

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