Squaric acid difluoride
M. Senzlober, H. Bürger, R. Eujen, A. Gelessus and W. Thiel
J. Fluorine Chem.99, 99-104 (1999)
Hitherto unknown squaric acid difluoride (3,4-difluoro-3-cyclobutene-1,2-dione) (1a) has been synthesized in 71 % yield
by gas phase fluorination of squaric acid dichloride with KF at 250°C. (1a) has been
characterized by multinuclear NMR,
mass, IR and Raman spectra. The IR spectrum is in excellent agreement with its ab initio prediction (MP2, 6-311+G(2d,p)).
The vacuum thermolysis of (1a) at 700°C does not yield the expected decarbonylation product FCCF (2a) although the
precursor of the latter, F2CCCO, and three C3F4 isomers (propyne, allene, cyclopropene) which
are also found as decomposition products of (2a) have been identified.
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