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

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...

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Published inTetrahedron letters Vol. 44; no. 46; pp. 8513 - 8518
Main Authors Kirihara, Masayuki, Kakuda, Hiroko, Tsunooka, Makoto, Shimajiri, Akihiro, Takuwa, Tomofumi, Hatano, Akihiko
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 10.11.2003
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALKENYL ETHERS
SILOXYCYCLOPROPANES
FACILE SYNTHESIS
EXPANSION-CYCLIZATION REACTIONS
HYPERVALENT LAMBDA(N)-IODANE-MEDIATED FRAGMENTATION
BETA-KETO RADICALS
SYSTEMS
GENERATION
MANGANESE(III) 2-PYRIDINECARBOXYLATE
DERIVATIVES
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Summary: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. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2003.09.089