Proximity Effects. XLVIII. Aprotic Decomposition of 2-Phenylcyclooctanone p-Toluenesulfonylhydrazone and 3-Phenylcy Clooctanone p-Toluenesulf Onylhydrazone

The aprotic decompositions of 2-phenylcyclooctanone p-toluenesulfonylhydrazone (tosylhydrazone) and 3-phenylcyclooctanone tosylhydrazone, promoted by sodium methoxide, were studied. Hydrocarbon products formedfrom 2-phenylcyclooctanone tosylhydrazone (87% yield) were 1-phenylcyclooctene (18%), 3-phenylcyclooctene(42%), exo-2-phenyl-cis-bicyclo[3.3.0]octane (15%), endo-2-phenyl-cis-bicyclo[3.3.0]octane (4%), 2-phenylcis-bicyclo[5.1.0]octane (3%), exo-8-phenyl-cis-bicyclo[5.1.0]octane (17%), and benzylcycloheptane (1%).The decomposition of 3-phenylcyclooctanone tosylhydrazone gave a 49% yield of hydrocarbons: 3-phenylcyclooctene (40%), 4-phenylcyclooctene (38%), 3-phenyl-cis-bicyclo[3.3.0]octane (17%), 1-phenyl-cis-bicyclo[5.1.0]octane (1 %), and 3-phenyl-cis-bicyclo[5.1.0]octane (2%).