Abella Carlos A M, Benassi Mario, Santos Leonardo S, Eberlin Marcos N, Coelho Fernando
Laboratory of Synthesis of Natural Products and Drugs and the ThoMSon Mass Spectrometry Laboratory, Institute of Chemistry, State University of Campinas, UNICAMP, 13084-971 Campinas, SP, Brazil.
J Org Chem. 2007 May 25;72(11):4048-54. doi: 10.1021/jo062556w. Epub 2007 May 2.
Using direct infusion electrospray ionization mass and tandem mass spectrometric experiments [ESI-MS(/MS)], we have performed on-line monitoring of some reactions used to form Tröger's bases. Key intermediates, either as cationic species or as protonated forms of neutral species, have been intercepted and characterized. The role of urotropine as the methylene source in these reactions has also been accessed. Reaction pathways shown by ESI-MS(/MS) have been probed by gas-phase ion/molecule reactions, and an expanded mechanism for Tröger's base formation based on the mass spectrometric data has been elaborated.
通过直接注入电喷雾电离质谱和串联质谱实验[ESI-MS(/MS)]，我们对一些用于形成特罗格碱的反应进行了在线监测。关键中间体，无论是阳离子物种还是中性物种的质子化形式，都已被捕获并表征。同时也研究了乌洛托品在这些反应中作为亚甲基源的作用。ESI-MS(/MS)显示的反应途径已通过气相离子/分子反应进行了探究，并基于质谱数据阐述了一个扩展的特罗格碱形成机制。
