jo061946f_si_001.pdf (345.31 kB)
Synthesis, Mechanism of Formation, and Dynamics of a Highly Fluorinated Methylenecyclobutene
journal contribution
posted on 2007-03-02, 00:00 authored by Sudharsanam Ramanathan, David M. LemalTreatment 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.