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Synlett 2000; 2000(8): 1135-1136
DOI: 10.1055/s-2000-6755
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Photochemical Carbon Skeletal Rearrangement of Vinylogous Baylis-Hillman Products: Direct Cyclopentene Cyclizations

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 photoreactions of vinylogous Baylis-Hillman products give in some cases cyclopentene derivatives, rather than dihydrofuran and cyclopropane derivatives generally observed in non-vinylogous Baylis-Hillman products. The positions for C-C bond formation depend on the stability of the radical intermediates.

vinylogous Baylis-Hillman product - cyclopentene cyclization - photochemical rearrangement - Di-π-methane rearrangement