Synthesis, mechanism of formation, and dynamics of a highly fluorinated methylenecyclobutene.
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 degrees 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.
Ramanathan
Sudharsanam
S
Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA.
Lemal
David M
DM