Issue 31, 2021

Diverse reactions of a fluorostannylenoid towards ethynes

Abstract

Fluoro(dialkyl)stannylenoid 2 exhibits unique reactivity towards ethynes with acetylenic hydrogen and those with trimethylsilyl groups, though the corresponding free dialkylstannylene 1 is inactive against those ethynes. Stannylenoid 2 reacts smoothly with gaseous ethyne and phenylethyne at room temperature, giving the corresponding diethynylstannanes, di(phenylethynyl)stannane 3 and diethynylstannane 6, respectively, in good yields with the concomitant evolution of H2. Trimethylsilyl-substituted ethynes such as 1-trimethylsilyl-(2-phenyl)ethyne and 1,2-bis(trimethylsilyl)ethyne react similarly to give 3 and bis(trimethylsilylethynyl)stannane 8, respectively. Rather unexpectedly, the reaction of 2 with (trimethylsilyl)ethyne affords 1,2-bis(ethenylstannyl)ethyne 7 in a good yield. The reactions of 2 with methyl and ethyl propynoates give the same products 4 and 5 as those obtained during the reaction of dialkylstannylene 1 without CsF. Pathways involving the nucleophilic attack of cesium acetylide to an ethyne-complexed stannylene were proposed, while the detailed mechanisms remain unknown. The structure of 7 was studied by single crystal X-ray diffraction analysis.

Graphical abstract: Diverse reactions of a fluorostannylenoid towards ethynes

Supplementary files

Article information

Article type
Paper
Submitted
10 jun 2021
Accepted
02 jul 2021
First published
02 jul 2021

Dalton Trans., 2021,50, 10806-10810

Diverse reactions of a fluorostannylenoid towards ethynes

L. Yan, C. Yan, J. Xu, L. Yang, G. Bian, L. Wang, M. Kira and Z. Li, Dalton Trans., 2021, 50, 10806 DOI: 10.1039/D1DT01914G

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