Mild Oxidation of Diarylacetylenes to 1,2-Diketones Using Oxone in Trifluoroacetic Acid

被引:41
作者
Chu, Jean-Ho [1 ]
Chen, Yen-Ju [2 ]
Wu, Ming-Jung [1 ]
机构
[1] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan
[2] Kaohsiung Med Univ, Fac Med & Appl Chem, Kaohsiung 807, Taiwan
来源
SYNTHESIS-STUTTGART | 2009年 / 13期
关键词
diarylalkyne; Oxone; oxidation; 1,2-diketone; ALPHA-DIKETONES; CROSS-LINKING; PHOTOCHEMICAL TRANSFORMATION; POLYSTYRENE COPOLYMERS; EFFICIENT SYNTHESIS; STYRENE COPOLYMER; PENDANT GROUPS; ALKYNES; BENZILS; CONVENIENT;
D O I
10.1055/s-0029-1216800
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of 1,2-diaryldiketones were synthesized in 15-90% yields by treatment of diarylacetylenes with Oxone as the oxidant in trifluoroacetic acid. Oxidation of 1-nitro-2-(phenylethynyl)benzene and 2,4'-(ethyne-1,2-diyl)bis(nitrobenzene) furnished 1-benzoylbenzo[c]isoxazol-3(1H)-one and benzo[c]isoxazol-3-yl(4-nitrophertyl)methanone as the major products, respectively.
引用
收藏
页码:2155 / 2162
页数:8
相关论文
共 37 条
[11]   An efficient route to 4-aryl-5-pyrimidinylimidazoles via sequential functionalization of 2,4-dichloropyrimidine [J].
Deng, XH ;
Mani, NS .
ORGANIC LETTERS, 2006, 8 (02) :269-272
[12]   Microwave-assisted efficient synthesis of 1,2-diaryldiketones:: a novel oxidation reaction of diarylalkynes with DMSO promoted by FeBr3 [J].
Giraud, Anne ;
Provot, Olivier ;
Peyrat, Jean-Francois ;
Alami, Mouad ;
Brion, Jean-Daniel .
TETRAHEDRON, 2006, 62 (33) :7667-7673
[13]   Synthesis and antiprotozoal activity of some new synthetic substituted quinoxalines [J].
Hui, X ;
Desrivot, J ;
Bories, C ;
Loiseau, PM ;
Franck, X ;
Hocquemiller, R ;
Figadère, B .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (04) :815-820
[14]   Synthesis, photoperoxidation and crosslinking of styrene copolymer with pendant benzil moieties [J].
Husar, B. ;
Lukac, I. .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2008, 195 (2-3) :191-197
[15]   Carbon tetrachloride as a thermoporometry liquid probe to study the cross-linking of styrene copolymer networks [J].
Husár, B ;
Commereuc, S ;
Lukác, I ;
Chmela, S ;
Nedelec, JM ;
Baba, M .
JOURNAL OF PHYSICAL CHEMISTRY B, 2006, 110 (11) :5315-5320
[16]   Synthesis of heteroaryl 1,2-diketones [J].
Katritzky, AR ;
Zhang, DZ ;
Kirichenko, K .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3271-3274
[17]   A novel method of synthesis of 1,2-diketones from 1,2-diols using N-bromosuccinimide [J].
Khurana, JM ;
Kandpal, BM .
TETRAHEDRON LETTERS, 2003, 44 (26) :4909-4912
[18]   Photooxidation of benzil groups in the presence of hindered amine stabilizers in the polystyrene film [J].
Kósa, C ;
Mosnácek, J ;
Lukác, I ;
Hrdlovic, P ;
Chmela, S ;
Habicher, WD .
JOURNAL OF APPLIED POLYMER SCIENCE, 2006, 100 (06) :4420-4428
[19]   Photochemical transformation of benzil pendant groups of polystyrene copolymers into benzoyl peroxide moieties and their subsequent thermal decomposition.: Cross-linking or chain scission? [J].
Kósa, C ;
Lukác, I ;
Weiss, RG .
MACROMOLECULES, 2000, 33 (11) :4015-4022
[20]   An efficient method for catalytic asymmetric reduction of diketones and application of synthesis to chiral 2,5-diphenylpyrrolidine and 2,5-diphenylthiolane [J].
Li Xiang ;
Zhao Gang ;
Cao Wei-Guo .
CHINESE JOURNAL OF CHEMISTRY, 2006, 24 (10) :1402-1405