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