Oxidation of Isodiphenylfluorindine: Routes to 13-Oxoisodiphenylfluorindinium Perchlorate and Fluorindine Cruciform Dimers

Georgia A Zissimou; Andreas Kourtellaris; Panayiotis A Koutentis

doi:10.1021/acs.orglett.7b03998

Oxidation of Isodiphenylfluorindine: Routes to 13-Oxoisodiphenylfluorindinium Perchlorate and Fluorindine Cruciform Dimers

Org Lett. 2018 Feb 2;20(3):844-847. doi: 10.1021/acs.orglett.7b03998. Epub 2018 Jan 19.

Authors

Georgia A Zissimou¹, Andreas Kourtellaris¹, Panayiotis A Koutentis¹

Affiliation

¹ Department of Chemistry, University of Cyprus , P.O. Box 20537, 1678 Nicosia, Cyprus.

PMID: 29350037
DOI: 10.1021/acs.orglett.7b03998

Abstract

Isodiphenylfluorindine (5) reacts with K₂Cr₂O₇/H⁺ to give 13-oxoisodiphenylfluorindinium perchlorate (7) (75%), but with phenyliodine bis(trifluoroacetate) (PIFA) or MnO₂ it gives the zwitterionic and quinoidal cruciform 13,13'-dimers 11 (85%) and 12 (89%), respectively. The zwitterionic 13,13'-dimer 11 can be rapidly converted with MnO₂ into the quinoidal 13,13'-dimer 12 (100%). UV-vis, NMR, single-crystal X-ray diffraction, and density functional theory studies support the structural assignments of all products. The electrochemical behavior of the compounds is also presented.

Publication types

Research Support, Non-U.S. Gov't