Bulletin of the Korean Chemical Society

  • 제13권1호
  • /
  • Pages.41-45
  • /
  • 1992
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Regioselectivity in the Cycloaddition Reactions of t-Butyl Trimethylsilyl Thioketone with 1,3-Butadienes

  • Kang, Kyung-Tae (Department of Chemical Education, Pusan National University) ;
  • Park, Chi-Hyo (Department of Chemical Education, Pusan National University) ;
  • Yoon, Ung-Chan (Department of Chemistry, Pusan National University)
  • 발행 : 1992.02.20
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초록

Thermal cycloaddition of t-butyl trimethylsilyl thioketone (1) with 2-substituted dienes such as isoprene and 2-trimethylsilyloxy-1,3-butadiene occurred smoothly at 80${\circ}C$ to afford regioiomeric mixtures of cycloadducts. On the other hand, similar treatment of 1 with 1-substituted dienes such as trans-1,3-pentadiene, 1-methoxy-and 1-acetoxy-1,3-butadiene and Danishefsky's diene afforded a single regioisomeric adduct, respectively. Protodesilylation of the silylated adducts 8 and 11 could also be performed with ease.

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참고문헌

  1. J. Chem. Soc. Perkin. Trans. v.1 G. Barbaro;A. Battaglia;P. Giorgianni;G. Maccagnani;D. Macciantolli
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  13. J. Am. Chem. Soc. v.96 S. Danishefsky;T. Kitahara
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피인용 문헌

  1. Synthesis and Properties of Secondary Thiocarbamoylsilanes vol.83, pp.1, 2010, https://doi.org/10.1246/bcsj.20090231