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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