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Trimethoxyarene as a Highly Ionizable Tag for Reaction Analysis by Atmospheric Pressure Photoionization Mass Spectrometry (APPI/MS): Exploration of Heterocyclic Synthesis
Author(s) -
Bui The Thuong Mathieu,
Catala Cédric,
Colas Cyril,
Schaeffer Christine,
Van Dorsselaer Alain,
Mann André,
Wagner Alain
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100919
Subject(s) - chemistry , photoionization , mass spectrometry , molecule , atmospheric pressure , ionization , mass spectrum , analytical chemistry (journal) , chromatography , ion , organic chemistry , oceanography , geology
A mass spectrometry (MS) method was developed to rapidly analyze crude reaction mixtures. This method relies on highly effective ionization by atmospheric pressure photoionization (APPI) of molecules with a prosthetic trimethoxyarene (TMOA) residue. In a crude reaction mixture, products resulting from the reaction of the TMOA‐labeled substrate will be selectively ionized to afford an easily readable mass spectrum. Interestingly, we noticed that TMOA‐labeled molecules were not fragmented and gave the preferred [M + H] + ion peak. This APPI‐MS reaction mixture analysis method was used for the optimization of heterocycle synthesis. By comparing results obtained by APPI/MS, GC, and HPLC analysis, it appeared that a semi‐quantification could be achieved by integrating the MS peak intensities.