The purpose of this research is ultimately to investigate the solvolytic outcome of trans sulfonates of 3,4-bis(trimethylsilyl)cyclbutane-1,2-diol, 1 as a possible means of silyl assisted bridging to form high energy strained systems. Previous literature has described the preparation of isomers of 1. Consequently, initial attempts toward its preparation involve modification of a previously described literature synthesis for the cisisomer. Synthesis is being attempted as a means of preparation of compound 2. The trans diol could potentially be prepared either as a product of the reduction of the dione or directly from the cis isomer. Using gamma-silyl promoted bridging, the molecule has the potential to bridge twice, producing a high strained hydrocarbon.

Synthesis of all-trans cyclobutyl systems

251st National Meeting (2016)

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