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2020 EJRNL PP Maxwell Gargiulo Holl -1.pdf
Terbatas Irwan Sofiyan
» ITB

In this Account, we chronicle our tortuous but ultimately fruitful quest to synthesize a [C?F?C]+ fluoronium ion in solution, thus providing the last piece of the organic halonium ion puzzle. Inspiration for the project can be traced all the way back to the graduate career of the corresponding author, wherein the analogy between a [C?H? C]+ “hydrido” bridge and a hypothetical [C?F?C]+ bridge was first noted. The earliest attempt to construct a bicyclo[5.3.3]tridecane-based fluoronium ion (based on the analogous hydrido bridged cation) proved to be synthetically difficult. A subsequent attempt involving a 1,8-substituted naphthalene ring was theoretically naiv? e in retrospect ....