Synthesis, Characterization, and Functionalization of 1‐Boraphenalenes
- Resource Type
- Authors
- Rachel J. Kahan; Daniel L. Crossley; Jessica Cid; James E. Radcliffe; Michael J. Ingleson
- Source
- Angewandte Chemie (International Ed. in English)
Angewandte Chemie International Edition
Kahan, R J, Crossley, D L, Cid, J, Radcliffe, J E & Ingleson, M J 2018, ' Synthesis, Characterization, and Functionalization of 1-Boraphenalenes ', Angewandte Chemie International Edition, vol. 57, no. 27, pp. 8084-8088 . https://doi.org/10.1002/anie.v57.27
Kahan, R J, Crossley, D L, Cid, J, Radcliffe, J E & Ingleson, M J 2018, ' Synthesis, Characterization, and Functionalization of 1-Boraphenalenes ', Angewandte Chemie-International Edition, vol. 57, no. 27, pp. 8084-8088 . https://doi.org/10.1002/anie.201803180
- Subject
- Borylation
010405 organic chemistry
phenalenyl
Communication
polycyclic aromatic hydrocarbons
General Medicine
aromaticity
010402 general chemistry
boron
01 natural sciences
Communications
3. Good health
0104 chemical sciences
- Language
- English
- ISSN
- 1521-3773
1433-7851
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.