Synthesis 2014; 46(01): 42-48
DOI: 10.1055/s-0033-1338550
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Thianthrene Derivatives Linked by Carbon Chains

Md. Chanmiya Sheikh*
Department of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan   Fax: +81(76)4456850   Email: chansheikh@yahoo.com   Email: yosimura@eng.u-toyama.ac.jp   Email: moritah@pb.ctt.ne.jp
,
Takasi Iwasawa
Department of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan   Fax: +81(76)4456850   Email: chansheikh@yahoo.com   Email: yosimura@eng.u-toyama.ac.jp   Email: moritah@pb.ctt.ne.jp
,
Akitaka Nakajima
Department of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan   Fax: +81(76)4456850   Email: chansheikh@yahoo.com   Email: yosimura@eng.u-toyama.ac.jp   Email: moritah@pb.ctt.ne.jp
,
Atsutaka Kitao
Department of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan   Fax: +81(76)4456850   Email: chansheikh@yahoo.com   Email: yosimura@eng.u-toyama.ac.jp   Email: moritah@pb.ctt.ne.jp
,
Noritatsu Tsubaki
Department of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan   Fax: +81(76)4456850   Email: chansheikh@yahoo.com   Email: yosimura@eng.u-toyama.ac.jp   Email: moritah@pb.ctt.ne.jp
,
Ryuta Miyatake
Department of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan   Fax: +81(76)4456850   Email: chansheikh@yahoo.com   Email: yosimura@eng.u-toyama.ac.jp   Email: moritah@pb.ctt.ne.jp
,
Toshiaki Yoshimura*
Department of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan   Fax: +81(76)4456850   Email: chansheikh@yahoo.com   Email: yosimura@eng.u-toyama.ac.jp   Email: moritah@pb.ctt.ne.jp
,
Hiroyuki Morita*
Department of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan   Fax: +81(76)4456850   Email: chansheikh@yahoo.com   Email: yosimura@eng.u-toyama.ac.jp   Email: moritah@pb.ctt.ne.jp
› Author Affiliations
Further Information

Publication History

Received: 16 July 2013

Accepted after revision: 02 October 2013

Publication Date:
07 November 2013 (online)


Abstract

Dithianthren-1-ylmethanol and 1,1′-methylenedithianthrene were prepared and their reactions were studied. Lithiation of 1,1′-methylenedithianthrene took place on the methylene carbon rather than on the thianthrene framework, and when the lithiated derivative was allowed to react with thianthren-1-ylcarbaldehyde, sterically hindered 1,2,2-trithianthren-1-ylethanol was obtained in good yield. The structures of 1,1′-methylenedithianthrene and 1,2,2-trithianthren-1-ylethanol were confirmed by X-ray crystallography. To clarify the nature and reactivity of thianthrene derivatives, we also prepared 1,6-(thianthren-1,9-diyl)hexane-1,6-diol (5,6,7,8,9,10-hexahydro-1,14-epithiodibenzo[b,j]thiacycloundecine-5,10-diol) as a model compound in which the 1- and 9-positions of thianthrene are bridged by a carbon chain.

 
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