Synthesis and thermal rearrangement of pentacyclo[6.5.0.04,12.05,10.09,13]trideca-2,6-diene

Article abstract of DOI:10.1016/0040-4020(95)00754-V

Pentacyclo[6.5.0.0^4,12.0^5,10.0^9,13]trideca-2,6-diene (16) has been synthesized in five steps from 1-hydroxyhexacyclo[6.5.0.0^2,6.0^3,11.0^5,10.0^9,12]trideca n-7-one (10). Compound 16 undergoes thermal rearrangement to pentacyclo[7.4.0.0^2,6.0^3,11.0^5,10]trideca-7,12-diene (i.e. '[2.2.1]triblattadiene', 19). The intermediacy of cis,cisoid,cis-tricyclo[7.4.0.0^2,7[trideca-3,5,10,12-tetraene (18) in the thermal rearrangement of 16 was inferred via analysis of the ¹H NMR spectrum of partially rearranged 16 and subsequently was further established via the results of a trapping experiment (i.e., fluorene was produced when thermal rearrangement of 16 was performed in the presence of 10% Pd/C).