Synthesis and Characterization of Isodiphenylfluorindone and Isodiphenylfluorindinone

J Org Chem. 2018 Apr 20;83(8):4754-4761. doi: 10.1021/acs.joc.8b00554. Epub 2018 Apr 5.

Abstract

Isodiphenylfluorindone 6 and isodiphenylfluorindinone 7 are synthesized. The former reacts with NaOMe to give the 13-methoxyisodiphenylfluorindone 22 (95%), while the latter reacts with 70% perchloric acid to give the bisperchlorate 21 (87%) and with MnO2 dimerizes to give 13,13'-bi(isodiphenylfluorindone) 4 (60%). UV-vis, NMR, CV, and DFT computational studies support the structural assignments of all products. Single-crystal X-ray diffraction studies are reported for isodiphenylfluorindinone 7.