Ring-opening fluorination and ring-expansion fluorination of cyclopropanemethanols with amine/metal fluoride/poly(hydrogen fluoride)-pyridine complex.

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概要

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• Treatment of cyclopropanemethanols with pyridinium poly(hydrogen fluoride) in the presence of diisopropylamine and KHF<SUB>2</SUB> 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.

• 公益社団法人 日本化学会の論文

著者

• Yoshioka Hirosuke

  The Institute of Physical and Chemical Research (RIKEN)

• Shimizu Makoto

  The Institute of Physical and Chemical Research (RIKEN)

• Kanemoto Shigekazu

  The Institute of Physical and Chemical Research (RIKEN)

関連論文

• Ring-opening fluorination and ring-expansion fluorination of cyclopropanemethanols with amine/metal fluoride/poly(hydrogen fluoride)-pyridine complex.

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