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THE UNEXPECTED FORMATION AND STRUCTURE OF 4,6-DIMETHYLTHIENO[3,4-C]THIOPHENE-1(3H)-THIONE

  作者 TICE NATHAN C; PEAK SARAH M; PARKIN SEAN  
  选自 期刊  Heterocycles;  卷期  2010年81-10;  页码  2229-2237  
  关联知识点  
 

[摘要]The reaction of 2,5-dimethylthiophene-3,4-dicarboxaldehye (1) with excess Lawesson's Reagent afforded the unexpected 5,5-fused ring thienothione derivative, 4,6-dimethylthieno[3,4-c]thiophene-1(3H)-thione (2), in good yield (79%). The desired non-classical thiophene, 1,3-dimethylthieno[3,4-c]thiophene (3), was observed by GC/MS as a minor product (approximately 5%) along with thione 2. The thienothione 2 was characterized spectroscopically and its structure was confirmed by X-ray crystallography. The formation of compound 2 is proposed to occur through a 1,3-hydride shift.

 
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