Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Reaction of Di-s-butoxyborane in Tetrahydrofuran with Selected Organic Compounds containing Representative Functional Groups. Catalytic Effect of Tetraalkoxyborate on the Reaction of Dialkoxyborane$^\dag$

  • Cha, Jin-Soon (Department of Chemistry, College of science, Yeungnam University) ;
  • Lee, Jae-Cheol (Department of Chemistry, College of science, Yeungnam University) ;
  • Kim, Jin-Euog (Department of Chemistry, College of science, Yeungnam University) ;
  • Lee, Kwang-Woo (Department of Chemistry, College of science, Yeungnam University) ;
  • Yoon, Mal-Sook (Department of Chemistry, College of science, Yeungnam University)
  • Published : 1987.08.20
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Abstract

The approximate rate and stoichiometry of the reaction of excess di-s-butoxyborane with selected organic compounds containing representative functional groups under standardized conditions (tetrahydrofuran, $25^{\circ}C)$ were examined in order to define the characteristics of the reagent for selective reductions. And the catalytic effect of lithium tetra-s-butoxyborate on the reaction of di-s-butoxyborane was also studied in order to increase the utility of this reducing system. Di-s-butoxyborane reacts only with simple aldehydes. However the addition of 2.5 mole % of lithium tetra-s-butoxyborate shows the tremendous rate enhancement of reaction for aldehydes, ketones, anhydrides, acid chlorides, lactones, and epoxides. This catalytic effect is assumed to in situ formation of lithium trialkoxyborohydride.

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References

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