We've found that munchone (1), formed by the in-situ dehydration of the corresponding amino acid (in benzene) undergoes a cycloaddition with epoxynaphthalene (2) to give adduct (3). We have not been able to isolate this adduct (yet) but have oserved the formation of (6) by NMR. Adduct (4), formed by the facile loss of CO2 is a second 1,3-dipole. This may react by one of two routes: Route a, to form compound (5) - which would be a nice route to a substituted pentacene, or: Route b, to give compound (6). Compound (6), although isolated, has never been fully characterized, as it is a mixture of isomers. We have, however, dehydrated (6) to give 1,3-diphenyl-2-benzylbenz[f]isoindole.
Efforts were directed at improving the yield of this reaction (3% overall at present) and exploring the chemistry of this new benz[f]isoindole. Additionally, we investigated the synthesis of other variously substituted benz[f]isoindoles from different munchnones and variously substituted epoxynaphthalenes and bridged imino-naphthalenes.
The eventual goal of this project was to prepare substituted polycyclic aromatic hydrocarbons for use in carenogenisis studies, and as potential organic optical or electrical conducting substances. Please email dhb@alum.dartmouth.org for more information.