Synthesis of Thianthrene Derivatives Linked by Carbon Chains

Md. Chanmiya Sheikh; Takasi Iwasawa; Akitaka Nakajima; Atsutaka Kitao; Noritatsu Tsubaki; Ryuta Miyatake; Toshiaki Yoshimura; Hiroyuki Morita

doi:10.1055/s-0033-1338550

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(01): 42-48
DOI: 10.1055/s-0033-1338550

paper

Synthesis of Thianthrene Derivatives Linked by Carbon Chains

Autor*innen

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

Abstract

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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.

Key words

heterocycles - polycycles - macrocycles - sulfur

Volltext

Referenzen

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