Oxidative Intramolecular Cyclization of Diketoximes: Synthesis of 1,5-Dinitro-cis-bicyclo[3.3.0]octane

摘要

The reactivities of the substrates were observed to fall into three distinct reactivity categories in which both, neither, or only one of cyclization methods was successful. Both methods were successful in generating 1,5-dinitro-cis-bicyclo[3.3.0]octane from the appropriate cyclooctane precursor. The dl/meso-2,6-dinitroheptanes could be successfully cyclized to a mixture of stereoisomeric 1,2-dimethyl-1,2-dinitrocyclopentanes while the corresponding dioxime strategy failed. Neither method was successful for the majority of the substrates examined. Studies to elucidate the reasons for these differences in reactivity are continuing.