| Herein we wish to report our approaches towards the synthesis of transition metal 5 and 6-member ortho-quinone methide analogs. Ortho-quinone methide intermediates are synthetically and biologically important. These interesting compounds have shown their usefulness in industrial, medical, and synthetic applications.;One of the more interesting aspects of quinone methides is their ability to alkylate DNA, and as a result, are used in many modern chemotherapeutic and antitumor drugs. But this ability is not limited to just pharmological applications. Their use is unprecedented in oil field applications as synthetic dispersants and in organic synthesis where they are used in [4+2] hetero-Diels Alder cycloaddition reactions.;This report will focus on the study and synthesis of varying 5-member non annulated and 6-member benzannulated quinone methides analogs that will be developed from known chemistry of lithiovinylallene systems. These lithiovinallene systems upon attachment to CpFe(CO)2I form sigma complexes that, when introduced to electrocyclic ring closure conditions ie. heat and/or hv, afford quinone methide analogs.;Also included in this report will be the discovery of the unique chemistry associated with lithium-halogen exchanges of substituted gem-dihalocyclopropanes and vinyl iodides. |
