Tetrahedrane is the last solid platonic hydrocarbon that has not been synthesized. However, if it could be prepared the molecule would be at a very high energy ground state, therefore the ΔH of combustion would be large and it could be a potentially high energy fuel. The purpose of this project is to investigate a potential synthetic pathway to methoxytetrahedrane, utilizing the gamma-silyl effect to accomplish a key transformation. Our proposed route is outlined in Scheme 1. Step one is to synthesize dibromoacetal 2, from trimethylsilylcylcobutanone 1, which could then be coupled using Zn resulting in bicyclobutane 3. Finally, bicyclobutane 3 could be treated with acid to generate the gamma silyl substituted ion, which would hopefully bridge upon silyl elimination to form methoxytetrahedrane 4.

Synthesis of methoxytetrahedrane by coupling and elimination of dibromosilylcylcobutane

253rd National Meeting (2017)

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