Bicyclobutanes exhibit significant ring strain.  Previous research has shown that the use of a trifluoromethyl group in the gamma position and trimethylsilyl group in the alpha postion of a cycloubutyl tosylate will result in gamma silyl elimination when a solvolysis is performed. The solvolysis yields ring-closure to the corresponding bicyclobutane product. This research aims to substitute CF<sub>3</sub> for other electron withdrawing groups, such as nitriles, carboxylic acids, and esters. The electron withdrawing group focused on in this research is the nitrile group. The initial protocol utilized in this research involved the use of a Wittig reaction to yield an exocyclic cyclubutyl alkene product from the ketone, to which different groups could be added.  Recently, this research has also been geared towards a employing a shorter synthesis for the preparation of cyanobicyclobutane <i>via</i> a cyanohydrin intermediate.

Synthesis of cyanobicyclobutane via the gamma silyl effect

251st National Meeting (2016)

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