658074-45-4Relevant academic research and scientific papers
Quadricyclane - Thermal cycloaddition to polyfluorinated carbonyl compounds: A simple synthesis of polyfuorinated 3-oxatricyclo[4.2.1.02,5]non-7-enes
Petrov, Viacheslav A.,Davidson, Frederic,Smart, Bruce E.
, p. 1543 - 1552 (2004)
Quadricyclane (1) readily undergoes [2+2+2] cycloaddition reactions with electron-deficient fluorinated carbonyl compounds to give polyfluorinated 3-oxatricyclo[4.2.1.02,5]non-7-enes in high yields. Hexfluoroacetone, trifluoroacetyl chloride, methyl trifluoropyruvate, α-(fluorosulfonyl)difluoroacetyl fluoride, and bis(trifluoromethyl)ketene all react rapidly with 1. Trifluoracetyl fluoride although less reactive, slowly interacts with 1 at ambient temperature. 1,1,1-Trifluoroacetone, trifluoroacetophenone, carbonyl fluoride, and CF3C(O)OC6F5 require higher temperatures (60-90 °C) for reaction, and ethyl trifluoroacetate is unreactive at 90 °C. Heating 1 with the ethyl hemiacetal of trifluoroacetaldehyde gives the corresponding cycloadduct of CF3C(O)H in 44% yield. The oxetane product from hexafluoroacetone is remarkably stable to both acids and bases, whereas the oxetanes with α-F or Cl leaving groups are sensitive to acid-catalyzed rearrangement.
Fluorinated monomers, fluorinated polymers having polycyclic groups with fused 4-membered heterocyclic rings, useful as photoresists, and processes for microlithography
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Page/Page column 11-12, (2008/06/13)
The present invention provides novel fluorine-containing copolymers which comprise at least one fluorinated olefin, at least one polycyclic ethylenically unsaturated monomer with a fused 4-membered heterocyclic ring and, optionally, other components. The copolymers are useful for photoimaging compositions and, in particular, photoresist compositions (positive-working and/or negative-working) for imaging in the production of semiconductor devices. The copolymers are especially useful in photoresist compositions having high UV transparency (particularly at short wavelengths, e.g., 157 nm) which are useful as base resins in resists and potentially in many other applications.
