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Synthesis of 4,6-Dimethyldibenzothiophene and 1,2,3,4-Tetrahydro-4,6-dimethyldibenzothiophene via Tilak Annulation

  作者 Xu, XY; Li, X; Wang, AJ; Sun, YY; Schweizer, WB; Prins, R  
  选自 期刊  Helvetica Chimica Acta;  卷期  2011年94-10;  页码  1754-1763  
  关联知识点  
 

[摘要]1,2,3,4-Tetrahydro-4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohexanone with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. A mixture of 1,2,3,4-tetrahydro-4,6-dimethyldibenzothiophene and 4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohex-2-en-1-one with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. 2-Bromo-3-methylcyclohexanone was synthesized by conjugate addition of Me(3)Al to 2-bromocyclohex-2-en-1-one with CuBr as catalyst and 2-bromo-3-methylcyclohex-2-en-1-one by bromination-elimination of 3-methylcyclohex-2-en-1-one. 1,2,3,4,4a,9b-Hexahydro-4,6-dimethyldibenzothiophene was prepared by reduction of 1,2,3,4-tetrahydro-4,6-dimethyldibenzothiophene with Zn and CF(3)COOH.

 
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