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Synthesis, Mechanism of Formation, and Dynamics of a Highly Fluorinated Methylenecyclobutene

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journal contribution
posted on 02.03.2007, 00:00 by Sudharsanam Ramanathan, David M. Lemal
Treatment of the hydrazone of 2H-perfluoro-2-methyl-3-pentanone with triethylamine at elevated temperatures yields a methylenecyclobutene via degradation to an acetylene followed by dimerization. The dimerization occurs even at −78 °C, and details of the reaction pathway have been elucidated. Both the acidity and the conformational dynamics of the methylenecyclobutene are influenced by buttressing effects in this crowded molecule.