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Synthesis 1994; 1994(1): 40-42
DOI: 10.1055/s-1994-25401
short paper
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Synthesis and Amine-Induced Ring-Opening of Silyl-Substituted Thiophene 1,1-Dioxides

S. Gronowitz* , A. -B. Hörnfeldt, E. Lukevics, O. Pudova
  • *Organic Chemistry 1, Chemical Center, University of Lund, Box 124, S-221 00 Lund, Sweden
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Publication Date:
17 September 2002 (online)

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Amine-induced ring-opening of the silylated thiophene 1,1-dioxides was used for the preparation of silyl-substituted dienes. Thus, the reaction of 2,5-dimethyl-3-trimethylsilylthiophene 1,1-dioxide (5) with piperidine at 100°C led to 3-trimethylsilyl-6-(1-piperidino)-(2Z,4E)-2,4-hexadiene (8) and the piperidine-induced ring-opening of 2-methyl-5-dimethylbutylsilylthiophene 1,1-dioxide gave 1-dimethylbutylsilyl-5-(1-piperidino)-(1E,3E)-1,3-pentadiene (9) as the main product.

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