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Some synthetic efforts in small ring chemistry
Cyclopropylcyclobutene was prepared via the intermediate
dicyclopropylcarbinyl carbene which was generated by the thermal
decomposition of the sodium salt of dicyclopropylketone p-toluenesulfonylhydrazone.
The successive thermal isomerization of cyclopropylcyclobutene
to 2-cyclopropyl-1, 3-butadiene and to vinylcyclopentene
was studied. Kinetic data were obtained for the cyclopropylcyclobutene
to 2-cyclopropyl-1, 3-butadiene isomerization in the gas
phase. Decomposition of the sodium salt was studied in different
solvent systems at 130°, but bicyclo(1.1.0)butane ring formation
was not a major reaction pathway under conditions similar to those
used in the decomposition of cyclopropylcarboxaldehyde p-toluenesulfonylhydrazone.
Attempts to synthesize the compounds bicyclo-(2.2.0)hex-1(4)-ene and bicyclo(2.2.0)hex-1-ene via carbenoid intermediates
were hampered by difficulties in preparing the necessary
precursors