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Synlett 1999; 1999(4): 411-412
DOI: 10.1055/s-1999-2653
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Fluorocyclization II. Cyclization of Methylthio Group Substituted Divinyl Ketones to 5-Fluorocyclopentenone Derivatives

Shoji Hara* , Satoru Okamoto, Masatoshi Narahara, Tsuyoshi Fukuhara, Norihiko Yoneda
  • *Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan; Fax +81-11-7 06-65 56; E-mail: hara@org-mc.eng.hokudai.ac.jp
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Publication Date:
31 December 1999 (online)

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In the presence of amine-HF complexes and Hg(OCOCF3)2, divinyl ketones having a methylthio group at the β-position cyclized to 5-fluorocyclopentenone derivatives selectively. The methylthio group at the β-position and alkyl substituents on the double bonds are a prerequisite to obtain the fluorocyclization products in good yields.

fluorocyclization - Nazarov reaction - fluorocyclopentenone - pyridine-6HF