Basheer Ahmad, Rappoport Zvi
Department of Organic Chemistry and the Lise Meitner Minerva Center for Computational Quantum Chemistry, The Hebrew University, Jerusalem 91904, Israel.
J Org Chem. 2008 Jan 4;73(1):184-90. doi: 10.1021/jo702083u. Epub 2007 Dec 12.
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, (1)H and (13)C 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.
16种酰胺烯醇与4-苯基-1,2,4-三唑啉-1,3-二酮的反应在固态和溶液中均生成开链加合物，而非带有半胺基部分的[2 + 2]环加合物。这一归属基于X射线晶体学、¹H和¹³C NMR数据以及红外光谱。提出的机理涉及在形式上的氧杂-烯反应中羟基质子的损失。讨论了机理细节和一种可能的替代情况。
