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

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

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
Volume44
Issue number46
DOIs
Publication statusPublished - 2003 Nov 10
Externally publishedYes

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Ethers
Fluorides
Electrons
Bearings (structural)
diethylaminosulfur trifluoride
cyclopropane
cyclopropanol

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Reaction of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride : The effects of substituents on the cleavage of the cyclopropane ring. / Kirihara, Masayuki; Kakuda, Hiroko; Tsunooka, Makoto; Shimajiri, Akihiro; Takuwa, Tomofumi; Hatano, Akihiko.

In: Tetrahedron Letters, Vol. 44, No. 46, 10.11.2003, p. 8513-8518.

Research output: Contribution to journalArticle

Kirihara, Masayuki ; Kakuda, Hiroko ; Tsunooka, Makoto ; Shimajiri, Akihiro ; Takuwa, Tomofumi ; Hatano, Akihiko. / Reaction of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride : The effects of substituents on the cleavage of the cyclopropane ring. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 46. pp. 8513-8518.
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