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2005
Oxetane derivatives
R 0035
Quadricyclane—Thermal Cycloaddition to Polyfluorinated Carbonyl Compounds. A Simple Synthesis of Polyfluorinated 3-Oxatricyclo[4.2.1.02,5]non08- 099 -7-enes.
— Perfluoroalkyl substituents have an unexpected and remarkable activating
effect on the carbonyl group and polyfluorinated carbonyl compounds are significantly
more reactive towards quadricyclane (I) than other carbonyl substrates. The order of
reactivity increases with the electron deficiency of the carbonyl group, cf. (IIa) > (IIb).
The greater reactivity of (VIa) compared to (IVf) is consistent with its relative electron-acceptor capocity. The formation of by-products in the reactions of (I) with (VI)
might be a result of competitive polar addition of (VI) to (I). With exception of (IIIb),
all new norbornenoxetanes are stable liquids at ambient temperature. — (PETROV*,
V. A.; DAVIDSON, F.; SMART, B. E.; J. Fluorine Chem. 125 (2004) 10, 1543-1552;
DuPont Cent. Res. Dev., Exp. Stn., Wilmington, DE 19880, USA; Eng.) —
H. Hoennerscheid
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