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37.3.1.1.7.4 Variation 4: Reaction of Fluorinated Carbonyl Compounds

DOI: 10.1055/sos-SD-037-00246

Griesbeck, A. G.; Sokolova, T.Science of Synthesis, (200837448.

The highly strained hydrocarbon tetracyclo[3.2.0.02,7.04,6]heptane (quadricyclane, 78) readily undergoes [2+2+2] cycloaddition reactions with electron-deficient fluorinated carbonyl compounds 79 such as hexafluoroacetone, trifluoroacetaldehyde, or trifluoroacetyl fluoride to give oxetanes 80 in high yields (44 to >95%, Scheme 30). Even the simplest substrate, carbonyl fluoride (COF2), results in a cycloaddition product in 48% yield when the reaction is carried out at elevated temperature (60°C) and autogenic pressure.[‌69‌]

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