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Synlett 1996; 1996(6): 481-492
DOI: 10.1055/s-1996-5467
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Organic Synthesis Utilizing 2-Phenylthiocyclobutyl Ketones1

Takeshi Takeda* , Tooru Fujiwara
  • *Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184, Japan, Fax 81 423 88 7034; E-mail takeda-t@cc.tuat.ac.jp
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Publication Date:
31 December 2000 (online)

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The organic synthesis utilizing 2-phenylthiocyclobutyl ketones, prepared by the [2+2] cycloaddition of 1-alkenyl sulfides with vinyl ketones, as starting materials are described. The preparations of 1-acetyl-1,3,5-cyclooctatrienes, hydrindanones, 4-acetylcyclohexenes, (Z)-enol trimethylsilyl ethers, and 1,1,5-trisubstituted (E)- and (Z)-1,5-dienes were achieved utilizing 1-cyclobutenyl ketones, prepared from 2-phenylthiocyclobutyl ketones by the oxidation and β-elimination of phenylthio group. The addition of organometallics to 2-phenylthiocyclobutyl ketones and following ring opening reactions also gave (E)- and (Z)-trisubstituted olefins having various functional groups with high stereoselectivity.

[2+2] cycloaddition - 2-phenylthiocyclobutyl ketone - 1-cyclobutenyl ketone - thionium ion - trisubstituted olefin

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