Oxa-ene reaction of enols of amides with 4-phenyl-1,2,4-triazoline-3,5-dione

被引:9
作者
Basheer, Ahmad [1 ,2 ]
Rappoport, Zvi [1 ,2 ]
机构
[1] Hebrew Univ Jerusalem, Dept Organ Chem, IL-91904 Jerusalem, Israel
[2] Hebrew Univ Jerusalem, Lise Meitner Minerva Ctr Computat Quantum Chem, IL-91904 Jerusalem, Israel
关键词
D O I
10.1021/jo702083u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The reaction of 16 enols of amides with 4-phenyl-1,2,4-triazoline-1,3-dione gave open chain adducts rather than the [2 + 2] cycloadducts with a hemiaminal moiety, both in solid state and in solution. This assignment is based on X-ray crystallography, H-1 and C-13 NMR data, and IR spectra. The suggested mechanism involves hydroxyl proton loss in a formal oxa-ene reaction. Mechanistic details and a possible alternative are discussed.
引用
收藏
页码:184 / 190
页数:7
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