Low-valent titanium induced simultaneous reduction of nitro group and S-S bond in nitrodisulfides: A novel method for the synthesis of benzothiazoline, benzothiazoles and 2,3-dihydro-1,5-benzothiazepines

Article abstract of DOI:10.1080/00397910008087072

The simultaneous reduction of nitro group and S-S bond in nitrodisulfides by TiCl₄/Sm system leds to the active intermediates 2, which were 'living' double-anions (nitride anions and sulfide anions) in situ. These new anion species reacted smoothly with aldehydes or ketones, acid chlorides or acid anhydrides and α,β-unsaturated ketones respectively to afford the desired benzothiazolines, benzothiazoles and 2,3-dihydro-1,5-benzothiazepines in good yields under mild and neutral conditions.

Full text of DOI:10.1080/00397910008087072

This article was downloaded by: [Fondren Library, Rice University ]
On: 14 November 2014, At: 12:44
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
Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
Low-valent Titanium Induced
Simultaneous Reduction
of Nitro Group and S-S
Bond in Nitrodisulfides:
A Novel Method For the
Synthesis of Benzothiazoline,
Benzothiazoles and 2,3-
Dihydro- 1,5-benzothiazepines
Weihui Zhong a , Xiaoyuan Chen a b & Yongmin Zhang
a
a Department of Chemistry , Zhejiang University
(Campus Xixi) , Hangzhou, 310028, P.R. China
b Department of Chemistry , Hunan Jishou
University , Jishou, 416000, P.R. China
Published online: 04 Dec 2007.
To cite this article: Weihui Zhong , Xiaoyuan Chen & Yongmin Zhang (2000) Low-
valent Titanium Induced Simultaneous Reduction of Nitro Group and S-S Bond in
Nitrodisulfides: A Novel Method For the Synthesis of Benzothiazoline, Benzothiazoles
and 2,3-Dihydro- 1,5-benzothiazepines, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 30:24, 4451-4460,
DOI: 10.1080/00397910008087072
To link to this article: http://dx.doi.org/10.1080/00397910008087072

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