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Communication | Special issue | Vol 44, No. 1, 1997, pp.75-80
Published online, 1st January, 1970
DOI: 10.3987/COM-96-S11
Synthesis of Highly Congested Bi- and Terthiophenes; 3,4,3',4'-Tetra-tert-butylbithiophene and 3',4'-Di-tert-butyl-2,2':5'2''-terthiophene

Juzo Nakayama,* Yo Ting, Yoshiaki Sugihara, and Akihiko Ishii

*Department of Chemistry, Faculty of Science, Saitama University, Saitama, Saitama 338-8570, Japan

Abstract

The Pd(PPh3)4-catalyzed coupling of 3,4-di-tert-butyl-2-thienylmagnesium bromide with 2-bromo-3,4-di-tert-butylthiophene gave 3,4,3’,4’-tetra-tert-butyl-2,2’-bithiophene (5) in moderate yield. X-Ray single crystal structure analysis of 5 revealed that its thiophene rings remain planer, but their plane is perpendicular to each other. The synthesis of 3’,4’-di-tert-butyl-2,2’:5’,2”-terthiophene in a similar way is also described.