Rosenau Thomas, Potthast Antje, Elder Tom, Kosma Paul
University of Agricultural Sciences, Institute of Chemistry, Muthgasse 18, A-1190 Vienna, Austria.
Org Lett. 2002 Nov 28;4(24):4285-8. doi: 10.1021/ol026917f.
[reaction: see text] The o-quinone methide (2) derived from vitamin E (1) can be stabilized at low temperatures in a complex with the highly polar N-methylmorpholine-N-oxide (5). The lifetime of 2 can thus be prolonged from less than 10 s to several minutes. In the complex formed, 2 adopts a zwitterionic, aromatic structure with the exocyclic methylene group in perpendicular arrangement to the ring plane, stabilized by the negatively charged oxygen in 5.
[反应：见正文] 源自维生素E（1）的邻醌甲基化物（2）在低温下可与高极性的N-甲基吗啉-N-氧化物（5）形成复合物而得以稳定。因此，2的寿命可从小于10秒延长至几分钟。在形成的复合物中，2呈现两性离子芳香结构，其环外亚甲基与环平面垂直排列，并由5中带负电荷的氧稳定。
