Issue 5, 2018

Synthesis of pyridine trans-tetrafluoro-λ6-sulfane derivatives via radical addition

Abstract

Pyridine tetrafluoro-λ6-sulfanes (SF4) with alkenyl or alkyl substituents have been synthesized for the first time via the radical addition reactions of pyridine-SF4 chlorides to alkynes or alkenes in good to high yields. X-Ray crystallographic analysis and DFT calculations disclosed an octahedral symmetrical trans-configuration of the hypervalent tetrafluorosulfanyl center. In contrast to phenyl-SF4 analogues, pyridine-SF4 compounds were found to be stable, which expands the utility of pyridine-SF4 compounds.

Graphical abstract: Synthesis of pyridine trans-tetrafluoro-λ6-sulfane derivatives via radical addition

Supplementary files

Article information

Article type
Research Article
Submitted
01 11 2017
Accepted
16 11 2017
First published
16 11 2017

Org. Chem. Front., 2018,5, 719-724

Synthesis of pyridine trans-tetrafluoro-λ6-sulfane derivatives via radical addition

P. Das, M. Takada, E. Tokunaga, N. Saito and N. Shibata, Org. Chem. Front., 2018, 5, 719 DOI: 10.1039/C7QO00994A

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