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Updated: Jun 13, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
Published on: March 20, 2017
Dilithioplumbole: a lead-bearing aromatic cyclopentadienyl analog
Masaichi Saito1, Masafumi Sakaguchi, Tomoyuki Tajima
1Department of Chemistry, Graduate School of Science and Engineering, Saitama University, Shimo-okubo, Sakura-ku, Saitama-city, Saitama, 338-8570 Japan. masaichi@chem.saitama-u.ac.jp
Abstract:
Although the concept of aromaticity has long played an important role in carbon chemistry, it has been unclear how applicable the stabilizing framework is to the heaviest elements. Here we report the synthesis of dilithiotetraphenylplumbole by reduction of hexaphenylplumbole. X-ray crystallography revealed a planar structure with no alternation of carbon-carbon bond lengths in the five-membered ring core. Nuclear magnetic resonance spectra and relativistic theoretical calculations show considerable aromatic character in the molecule, thus extending aromaticity to carbon's heaviest congener.
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