Formation of Furan Derivatives from Phenacyl Bromides and Sodium Telluride; Attempted Extension to Coumarin Synthesis
作者： Seetharamaiyer Padmanabhan , Takuji Ogawa , Hitomi Suzuki
DOI: 10.1246/BCSJ.62.2114
关键词:
摘要: The enolates, generated from phenacyl bromides by sodium telluride, yield 2,4-diarylfurans in addition to the expected dehalogenation products. No 1,4-dicarbonyl compounds could be isolated even presence of excess oxidizing agent, copper(II) chloride. Condensation 2-(methoxymethoxy)arenecarbaldehydes with ethyl bromoacetate telluride gave α,β-unsaturated esters which resisted cyclization desired coumarin derivatives. Attempted intramolecular Reformatsky-type reaction 2-(bromoacetoxy)benzaldehyde only 6,12-epoxy-6H,12H-dibenzo[b,f]-[1,5]dioxocin as major product.
csj.jp参考文章(10)
Hitomi Suzuki, Hajime Manabe, Takashi Kawaguchi, Masahiko Inouye, Reduction of Aromatic Nitro Compounds and Thioketones with Sodium Telluride under Aprotic Conditions Bulletin of the Chemical Society of Japan. ,vol. 60, pp. 771- 772 ,(1987) , 10.1246/BCSJ.60.771
J. L. Belletire, E. G. Spletzer, Oxidative Coupling. V. Carbon-Carbon Bond Formation From β-Ketosulfone Dianions Synthetic Communications. ,vol. 17, pp. 1701- 1707 ,(1987) , 10.1080/00397918708063987
Michael W. Rathke, Andreas Lindert, Reaction of ester enolates with copper(II) salts. Synthesis of substituted succinate esters Journal of the American Chemical Society. ,vol. 93, pp. 4605- 4606 ,(1971) , 10.1021/JA00747A051
Charles Allan Brown, Saline hydrides and superbases in organic reactions. VII. Potassium hydride, highly active new hydride reagent. Reactivity, applications, and techniques in organic and organometallic reactions Journal of Organic Chemistry. ,vol. 39, pp. 3913- 3918 ,(1974) , 10.1021/JO00940A025
Rawls H. Frazier, Richard L. Harlow, Oxidative coupling of ketone enolates by ferric chloride Journal of Organic Chemistry. ,vol. 12, pp. 5408- 5411 ,(1980) , 10.1021/JO01314A052
Yoshihiko Ito, Toshiro Konoike, Toshiro Harada, Takeo Saegusa, Synthesis of 1,4-diketones by oxidative coupling of ketone enolates with copper(II) chloride Journal of the American Chemical Society. ,vol. 99, pp. 1487- 1493 ,(1977) , 10.1021/JA00447A035
Charles Allan Brown, Saline hydrides and superbases in organic reactions. II. Facile reaction of potassium hydride with ketones. Rapid, quantitative formation of potassium enolates from ketones via kaliation Journal of Organic Chemistry. ,vol. 39, pp. 1324- 1325 ,(1974) , 10.1021/JO00923A042
F. B. LaForge, Rotenone. XXVI. Synthesis of the Parent Substances of Some Characteristic Rotenone Derivatives Journal of the American Chemical Society. ,vol. 55, pp. 3040- 3048 ,(1933) , 10.1021/JA01334A076
Reynold C. Fuson, Norman. Thomas, Extension of the Reformatsky Reaction to new Types of Compounds Journal of Organic Chemistry. ,vol. 18, pp. 1762- 1766 ,(1953) , 10.1021/JO50018A022
Roger Adams, M. F. Fogler, C. W. Kreger, THE STRUCTURE OF DISALICYL ALDEHYDE Journal of the American Chemical Society. ,vol. 44, pp. 1126- 1133 ,(1922) , 10.1021/JA01426A026