Ring-Opening Fluorination and Ring-Expansion Fluorination of Cyclopropanemethanols with Amine/Metal Fluoride/Poly(hydrogen fluoride)–Pyridine Complex

Treatment of cyclopropanemethanols with pyridinium poly(hydrogen fluoride) in the presence of diisopropylamine and KHF2 gave selectively homoallylic fluorides or fluorocyclobutanes according to the mode of substitution of the starting cyclopropanemethanols. Cyclopropanemethanols with no substitution...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 62; no. 6; pp. 2024 - 2031
Main Authors Kanemoto, Shigekazu, Shimizu, Makoto, Yoshioka, Hirosuke
Format Journal Article
LanguageEnglish
Published The Chemical Society of Japan 01.06.1989
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Summary:Treatment of cyclopropanemethanols with pyridinium poly(hydrogen fluoride) in the presence of diisopropylamine and KHF2 gave selectively homoallylic fluorides or fluorocyclobutanes according to the mode of substitution of the starting cyclopropanemethanols. Cyclopropanemethanols with no substitution at 1-position of the cyclopropane ring gave homoallylic fluorides in a stereoselective manner. While, 1-methylcyclopropanemethanol gave the fluorocyclobutane in high stereoselectivity. Fluorocyclobutanes containing hydroxy methyl group were also prepared from 2-(1-methylcyclopropyl)oxiranes. The amine and the metal fluoride were necessary as additives for the best results. Influencing factors involving solvents and temperature for the reactions are also described.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.62.2024