![Author ORCID: We display the ORCID iD icon alongside authors names on our website to acknowledge that the ORCiD has been authenticated when entered by the user. To view the users ORCiD record click the icon. [opens in a new tab]](https://chemrxiv.org/engage/assets/public/chemrxiv/images/logos/orcid.png)
Abstract
Previous gram-scale synthesis of 5,10-disilyldibenzo[a,e]pentalenes (5,10-disilylDBPs), which are good precursors of 5,10-dihaloDBPs, was accomplished by the reduction of trialkyl(phenylethynyl)silanes with highly pyrophoric potassium metals. Here we report two types of potassium-free and scalable synthesis of 5,10-disilylDBPs: (1) reduction of trialkyl(phenylethynyl)silanes with sodium dispersion (SD), and (2) reduction of trialkyl(phenylethynyl)silanes with lithium in the presence of NaOtBu. Both reactions involve 1,4-disodio-1,3-butadienes with an s-trans conformation as the key intermediates.
Supplementary materials
Title
Supporting Information
Description
Energetic comparison of 1,4-dimetallo-1,3-butadienes (Table S1), optimized structures and cartesian coordinates of 1,4-dimetallo-1,3-butadiens (Figure S1), and 1H NMR spectra for 2a,b and 4 (Figures S2–4).
Actions
