Synthesis, Characterization, and Functionalization of 1-Boraphenalenes

Rachel J. Kahan, Daniel L. Crossley, Jessica Cid, James E. Radcliffe, Michael J. Ingleson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

1-Boraphenalenes have been synthesized by reaction of BBr3 with 1-(aryl-ethynyl)naphthalenes, 1-ethynylnaphthalene, and 1-(pent-1-yn-1-yl)naphthalene and they can be selectively functionalized at boron or carbon to form bench-stable products. All of these 1-boraphenalenes have LUMOs localized on the planar C12B core that are closely comparable in character to isoelectronic phenalenyl cations. In contrast to the comparable LUMOs, the aromatic stabilization of the C5B ring in 1-boraphenalenes is dramatically lower than the C6 rings in phenalenyl cations. This is due to the occupied orbitals of π symmetry being less delocalised in the 1-boraphenalenes.

Original languageEnglish
Pages (from-to)8084-8088
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number27
Early online date11 May 2018
DOIs
Publication statusE-pub ahead of print - 11 May 2018

Keywords

  • aromaticity
  • boron
  • borylation
  • phenalenyl
  • polycyclic aromatic hydrocarbons

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