Cerium(IV) ammonium nitrate mediated addition of ethyl acetoacetate and dimethyl malonate to indene

被引:0
|
作者
Nair, V
Mathew, J
Mathen, JS
机构
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The oxidative addition of ethyl acetoacetate to indene mediated by cerium(IV) ammonium nitrate(CAN) leads to the formation of 2-(2'-indan-1'-one)3-oxobutanoic acid ethyl ester 7 along with two other products, the dihydrofuran 9 and the methyl ester 10. Similar addition of dimethyl malonate to indene gives the indanone 11 and the methyl ether 12. A tentative mechanism which rationalizes the formation of these products is proposed.
引用
收藏
页码:366 / 368
页数:3
相关论文
共 50 条
  • [41] DEMETHYLATION AND NITRATION OF ARYLDIMETHYLAMINES WITH CERIUM (IV) AMMONIUM-NITRATE
    GALLIANI, G
    RINDONE, B
    SCOLASTICO, C
    SYNTHETIC COMMUNICATIONS, 1975, 5 (05) : 319 - 323
  • [42] Mild and neutral deprotections catalyzed by cerium(IV) ammonium nitrate
    Maulide, Nuno
    Vanherck, Jean-Christophe
    Gautier, Arnaud
    Marko, Istvan E.
    ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (06) : 381 - 392
  • [43] Oxidative addition of 1,3-dicarbonyl compounds to alkenes mediated by cerium(IV) ammonium nitrate and manganese(III) acetate: A comparative study
    Nair, V
    Mathew, J
    Radhakrishnan, KV
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (12): : 1487 - 1492
  • [44] A novel synthesis of α-azidocinnamates, α-azido-α,β-unsaturated ketones and β-azidostyrenes mediated by cerium(IV) ammonium nitrate
    Nair, V
    George, TG
    TETRAHEDRON LETTERS, 2000, 41 (17) : 3199 - 3201
  • [45] Cerium(IV) ammonium nitrate mediated 5-endo-dig cyclization of α-amino allenylphosphonates to spirodienones
    Adler, Pauline
    Fadel, Antoine
    Rabasso, Nicolas
    CHEMICAL COMMUNICATIONS, 2015, 51 (17) : 3612 - 3615
  • [46] ortho-Amide-Directed Oxidation of Internal Aryl Alkynes Mediated by Cerium(IV) Ammonium Nitrate
    Su, Chieh-Fu
    Hu, Wan-Ping
    Vandavasi, Jaya Kishore
    Liao, Chao-Cheng
    Hung, Chen-Ya
    Wang, Jeh-Jeng
    SYNLETT, 2012, (14) : 2132 - 2136
  • [47] Carbon-heteroatom bond-forming reactions mediated by cerium(IV) ammonium nitrate: An overview
    Nair, V
    Panicker, SB
    Nair, LG
    George, TG
    Augustine, A
    SYNLETT, 2003, (02) : 156 - 165
  • [48] A direct synthesis of aryl thiocyanates using cerium(IV) ammonium nitrate
    Nair, V
    George, TG
    Nair, LG
    Panicker, SB
    TETRAHEDRON LETTERS, 1999, 40 (06) : 1195 - 1196
  • [49] DUALITY OF MECHANISM IN THE OXIDATION OF ALKENYLBENZENES BY CERIUM(IV) AMMONIUM-NITRATE
    BACIOCCHI, E
    ROL, C
    SEBASTIANI, GV
    ZAMPINI, A
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (18) : 1045 - 1047
  • [50] Cerium(IV) ammonium nitrate - A versatile single-electron oxidant
    Nair, Vijay
    Deepthi, Ani
    CHEMICAL REVIEWS, 2007, 107 (05) : 1862 - 1891