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

2007-03-02T00:00:00Z (GMT) 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.