Double dehydrogenation of carbocyclic β-dicarbonyl compounds:Koser's reagent can do what iodine(V) reagents can

被引:0
作者
Shan-Shan Liu [1 ,2 ]
Li Wang [3 ]
Ya-Nan Duan [1 ]
Ao Yu [3 ]
Chi Zhang [1 ]
机构
[1] State Key Laboratory of Elemento-Organic Chemistry,Collaborative Innovation Center of Chemical Science and Engineering (Tianjin),College of Chemistry,Nankai University
[2] Department of Chemical Engineering and Safety,Binzhou University
[3] Central Laboratory,College of Chemistry,Nankai University
基金
中国国家自然科学基金;
关键词
Koser’s reagent; double dehydrogenation; hypervalent twisting; 2,3-benzotropone; DFT calculations;
D O I
暂无
中图分类号
O621.25 [];
学科分类号
070303 ; 081704 ;
摘要
Koser’s reagent is found to be effective in the oxidative double dehydrogenation of various carbocyclic β-dicarbonyl compounds,which constitutes the first example on dehydrogenation reactivity of hypervalent iodine(Ⅲ) reagents for carbocyclic carbonyl compounds. DFT calculations reveal that the rate-determining step is the electrophilic addition of PhI+OH onto enolate of monodehydrogenated product.
引用
收藏
页码:597 / 601
页数:5
相关论文
共 5 条
  • [1] Koser, G. F,Rebrovic, L,Wettach, R. H. Journal of Organic Chemistry . 1981
  • [2] Zhdankin, V. V,Stang, P.J. Chemical Reviews . 2002
  • [3] Carman C S,Koser G.F. Journal of Organic Chemistry . 1983
  • [4] Koser GF. Advances in Heterocyclic Chemistry . 2003
  • [5] Herault X,Mc Nelis E. Tetrahedron . 1996