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Synlett 2000; 2000(4): 491-492
DOI: 10.1055/s-2000-6586
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Photochemical Carbon Skeletal Rearrangement of Cyclic Baylis-Hillman Products: Ring Contraction or Not? That is the Question

Koichi Mikami* , Yasutaka Okubo
  • *Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552, Japan
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Publication Date:
31 December 2000 (online)

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The photoreaction of seven-membered Baylis-Hillman products is shown to give 1,4-diketones without ring contraction under irradiation with high pressure mercury lamp. In sharp contrast, even a six-membered Baylis-Hillman product with γ,γ-disubstituent gives the ring contraction 1,4-diketone under the same conditions.

cyclic Baylis-Hillman product - ring contraction - photochemical rearrangement - 1,4-diketone