Reaction of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride: The effects of substituents on the cleavage of the cyclopropane ring

Masayuki Kirihara, Hiroko Kakuda, Makoto Tsunooka, Akihiro Shimajiri, Tomofumi Takuwa, Akihiko Hatano

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The reaction of tertiary cyclopropanol silyl ethers with diethylaminosulfur trifluoride usually causes ring opening to produce allylic fluorides. However, cyclopropyl silyl ethers bearing a strong electron-donating substituent at C1 or an electron-withdrawing substituent at C2 do not afford allylic fluorides but fluorocyclopropanes. It has also been proved that an electron-donating substituent at C2 of the tertiary cyclopropanol silyl ethers promotes ring opening in the reaction with diethylaminosulfur trifluoride.

Original languageEnglish
Pages (from-to)8513-8518
Number of pages6
JournalTetrahedron Letters
Issue number46
Publication statusPublished - 2003 Nov 10


ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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