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Synthesis, Characterization, and Functionalization of 1-Boraphenalenes.

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 C₁₂ B core that are closely comparable in character to isoelectronic phenalenyl cations. In contrast to the comparable LUMOs, the aromatic stabilization of the C₅ B ring in 1-boraphenalenes is dramatically lower than the C₆ rings in phenalenyl cations. This is due to the occupied orbitals of ? symmetry being less delocalised in the 1-boraphenalenes.

SUBMITTER: Kahan RJ

PROVIDER: S-EPMC6175385 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Synthesis, Characterization, and Functionalization of 1-Boraphenalenes.

Kahan Rachel J RJ Crossley Daniel L DL Cid Jessica J Radcliffe James E JE Ingleson Michael J MJ

Angewandte Chemie (International ed. in English) 20180606 27

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 C12 B core that are closely comparable in character to isoelectronic phenalenyl cations. In contrast to the comparable LUMOs, the aromatic stabilization of the C5</s ...[more]

PMID: 29750391

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