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

Prajwalita Das; Masahiro Takada; Etsuko Tokunaga; Norimichi Saito; Norio Shibata

doi:10.1039/C7QO00994A

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

Prajwalita Das,^a Masahiro Takada,^a Etsuko Tokunaga,

^a Norimichi Saito^b and Norio Shibata

*^a

Author affiliations

* Corresponding authors

^a Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
E-mail: nozshiba@nitech.ac.jp

^b Pharmaceutical Division, Ube Industries, Ltd., Seavans North Bldg., 1-2-1 Shibaura, Minato-ku, Tokyo 105-8449, Japan

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.

This article is part of the themed collections: Organic Chemistry Frontiers HOT articles for 2018 and Organic Chemistry Frontiers HOT articles for 2017

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C7QO00994A
Article type: Research Article
Submitted: 01 nov 2017
Accepted: 16 nov 2017
First published: 16 nov 2017

Download Citation

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic Chemistry Frontiers