Synthesis of Sumanene Hexatrifluoromethanesulfinate and exploring the extent of chemical reactivity of Sumanene and Hexakis(bromomethyl) sumanene

Abstract

Sumanene is a very interesting molecule especially owing to its unique structure. The extent of the chemical reactivity that the sumanene molecule can show is still a topic that is being heavily researched in the field of research of curved polyaromatic compounds. In this research thesis, the chemical reactivity of the sumanene molecule has been studied including the chemical reactivity of the benzylic and aromatic positions. Trails have been made to synthesize a molecular cage which includes the two sumanene bowls linked together by a diamino linker. However, due to the high complexity of the conditions that were required to be optimized, the attempt to synthesize it failed. Moving ahead with the hexaphosphonate derivative of sumanene, an opportunity appeared to try if a coupling reaction namely Horner–Wadsworth–Emmons reaction, which produces E and Z alkenes can be performed on it. When the reaction was tried with a strong base, competitive deprotonation of the benzylic proton was found along with the alpha proton adjacent to the phosphonate group. This result implied the fact that further attention should be paid to the acidity of those two protons and the basicity of the base used. Finally, the substitution reaction was tried on hexa-bromo sumanene in which the six bromo groups were substituted with six sulphate groups and the pure product was isolated in a decent yield followed by a trail to perform [2+1] cycloaddition of the formed product to the C60 fullerene.