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

被引：10

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 01期

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

页码：184 / 190

页数：7

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