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Synthesis 2001; 2001(1): 0063-0068
DOI: 10.1055/s-2001-9740
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Regioselective Allylation of 1,2-Naphthoquinones using Photoaddition Reaction with Allylsilanes: Synthesis of 3-Allyl-1,2-Naphthoquinones

Akio Takuwa* , Takahisa Sasaki, Hidetoshi Iwamoto, Yutaka Nishigaichi
  • *Department of Material Science, Faculty of Science and Engineering, Shimane University, Matsue 690-8504, Japan; Fax +81(852)32 64 29; E-mail: takuwa@riko.shimane-u.ac.jp
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Publication Date:
31 December 2001 (online)

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The photochemical reaction of 1,2-naphthoquinones with allylsilanes affords [3 + 2]photocycloadducts, which are converted to 3-allyl-1,2-naphthoquinones in moderate to good overall yields by treatment with boron trifluoride, ammonium cerium(IV) nitrate or tetrabutylammonium fluoride.

quinones - allylation - regioselectivity - photochemistry - ring opening