Letters in Organic Chemistry ( IF 0.8 ) Pub Date : 2020-07-31 , DOI: 10.2174/1570178617666200210111928 Andrew Karkhut 1 , Sviatoslav Polovkovych 1 , Roman Lesyk 2 , Volodymyr Novikov 1
The reaction of bis-(4,6-dichloro-[1,3,5]triazin-2-yl)-diazene with furan proceeds with the formation of inverse electron demand Diels-Alder product with a high yield. M06 2X/6 31G(d,p) calculations show thermodynamic instability of “normal” DA reaction product and predict its [3,3] sigmatropic rearrangement to the thermodynamically more favorable formal IEDDA reaction product. The obtained NMR spectra were in good agreement with GIAO calculations and were in accordance with DFT thermochemical data that confirmed the formation of the described product. IR and UV/Vis spectral data was also obtained and discussed.
中文翻译:
双(4,6-二氯-[1,3,5]三嗪-2-基)-二氮杂呋喃的区域选择性IED Diels-Alder反应及其分子机理
双-(4,6-二氯-[1,3,5]三嗪-2-基)-二氮杂与呋喃的反应以高收率形成反电子需求的Diels-Alder产物。M06 2X / 6 31G(d,p)计算显示出“正常” DA反应产物的热力学不稳定性,并预测了其[3,3]σ重排为热力学更有利的形式IEDDA反应产物。所获得的NMR光谱与GIAO计算非常吻合,并且符合证实所述产物形成的DFT热化学数据。还获得并讨论了IR和UV / Vis光谱数据。