Activation and facile dealkylation of monooxides of 1,8-bis(alkylthio)naphthalene and 2,2′-bis(alkylthio)biphenyl with triflic anhydride via dithiadications

Article abstract of DOI:10.1080/10426509708545586

Dithiadications bearing 1,8-bis(alkylthio)naphthalene 2A(a-e) and 2,2′-bis(alkylthio)biphenyl 2B(a-e) structure undergo either the facile deprotonation from the methyl group or dealkylation from the methylene groups by the triflate anion. Dications 2A(a) and 2B(a) having methyl groups were deprotonated readily to afford cyclic sulfonium salts 3A(a) and 3B(a). However, dithiadications 2A(b-e) and 2B(b-e) having ethyl, propyl, isopropyl and benzyl groups were readily dealkylated even at -45°C to give thiasulfonium salts 4A(b-e) and 4B(b-e) and alkyl triflates 5(a-e) in good yields. The intermediary formation of dithiadications 2A(a-e) and 2B(a-e) were confirmed by direct observation using NMR spectroscopy, D-labelled experiments and trapping experiments.

Full text of DOI:10.1080/10426509708545586

This article was downloaded by: [York University Libraries]
On: 29 December 2014, At: 09:43
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK
Phosphorus, Sulfur, and Silicon
and the Related Elements
Publication details, including instructions for authors
and subscription information:
http://www.tandfonline.com/loi/gpss20
Activation and Facile Dealkylation
of Monooxides of 1,8-
Bis(alkylthio)naphthalene and
2,2′-Bis(alkylthio)biphenyl
with Triflic Anhydride via
Dithiadications
Hidetaka Shima , Ryoji Kobayashi & Naomichi Furukawa
a
Tsukuba Advanced Research Alliance Center,
Department of Chemistry , University of Tsukuba ,
Tsukuba, Ibaraki 305, Japan
b
Tsukuba Advanced Research Alliance Center,
Department of Chemistry , University of Tsukuba ,
Tsukuba, Ibaraki 305, Japan
c
Tsukuba Advanced Research Alliance Center,
Department of Chemistry , University of Tsukuba ,
Tsukuba, Ibaraki 305, Japan
Published online: 17 Mar 2008.
To cite this article: Hidetaka Shima , Ryoji Kobayashi & Naomichi Furukawa (1997)
Activation and Facile Dealkylation of Monooxides of 1,8-Bis(alkylthio)naphthalene and
2,2′-Bis(alkylthio)biphenyl with Triflic Anhydride via Dithiadications, Phosphorus, Sulfur,
and Silicon and the Related Elements, 120:1, 437-438, DOI: 10.1080/10426509708545586
To link to this article: http://dx.doi.org/10.1080/10426509708545586
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information
(
&
the “Content”) contained in the publications on our platform. However, Taylor
Francis, our agents, and our licensors make no representations or warranties
whatsoever as to the accuracy, completeness, or suitability for any purpose
of the Content. Any opinions and views expressed in this publication are the
opinions and views of the authors, and are not the views of or endorsed by

Taylor & Francis. The accuracy of the Content should not be relied upon and
should be independently verified with primary sources of information. Taylor and
Francis shall not be liable for any losses, actions, claims, proceedings, demands,
costs, expenses, damages, and other liabilities whatsoever or howsoever caused
arising directly or indirectly in connection with, in relation to or arising out of the
use of the Content.
This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan, sub-
licensing, systematic supply, or distribution in any form to anyone is expressly
forbidden. Terms & Conditions of access and use can be found at http://
www.tandfonline.com/page/terms-and-conditions