Acetylenic and pyridyl bicyclobutanes are unusual systems that have potential medicinal applications. The objective was to synthesize substituted bicyclobutanes using electron withdrawing group (EWG) directed gamma silyl elimination to bridge compounds containing a variety of different leaving groups. A wide range of EWGs were investigated for bridging capability including: ethynyl, ethyl propiolyl, 2-fluropyridyl, and pyridyl. Solvolysis of the ethynyl system yielded substitution as seen by <sup>1</sup>H-NMR. The propiolyl precursor has been synthesized, but the outcome of solvolysis is still under investigation. Contrary to the ethynyl system, solvolysis as well as heating of 2-fluoropyridyryl trifluoroacetates appears to induce bicyclobutane formation, but only as a minor product. Improving the yields of the 2-fluoropyridyl-substituted bicyclobutane and solvolysis of the unsubstituted pyridyl system are still under investigation.

Synthesis of pyridyl and propiolyl bicyclobutanes

255th National Meeting (2018)

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