Gas-Phase Synthesis of 1-Silacyclopenta-2,4-diene

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• 作者：Dr. Tao Yang ; Dr. Beni B. Dangi ; Aaron M. Thomas ; Dr. Bing-Jian Sun ; Tzu-Jung Chou ; Prof. Dr. Agnes H. H. Chang and Prof. Dr. Ralf I. Kaiser
• 刊名：Angewandte Chemie International Edition
• 出版年：2016
• 出版时间：July 4, 2016
• 年：2016
• 卷：55
• 期：28
• 页码：7983-7987
• 全文大小：1622K
• ISSN：1521-3773

文摘

Silole (1-silacyclopenta-2,4-diene) was synthesized for the first time by the bimolecular reaction of the simplest silicon-bearing radical, silylidyne (SiH), with 1,3-butadiene (C₄H₆) in the gas phase under single-collision conditions. The absence of consecutive collisions of the primary reaction product prevents successive reactions of the silole by Diels–Alder dimerization, thus enabling the clean gas-phase synthesis of this hitherto elusive cyclic species from acyclic precursors in a single-collision event. Our method opens up a versatile and unconventional path to access a previously rather obscure class of organosilicon molecules (substituted siloles), which have been difficult to access through classical synthetic methods.