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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 26, Number 4
BKCSDE 26(4)
April 20, 2005 

Electrospray Ionization Mass Spectrometric Observation of Oligomers in Paal-Knorr Synthesis of 2,5-Dimethyl-1-phenylpyrrole
So-Young Park, Man-Seog Chun, Jin-Su Song, Hie-Joon Kim*
ESI MS, GC-MS, Paal-Knorr synthesis, 2,5-Dimethyl-1-phenylpyrrole, Oligomer
Electrospray ionization mass spectrometry (ESI MS) was used, along with gas chromatography-mass spectrometry (GC-MS), to monitor Paal-Knorr synthesis of 2,5-dimethyl-1-phenylpyrrole by condensation of aniline with 2,5-hexanedione. In addition to 2,5-dimethyl-1-phenylpyrrole observed as a single spot by TLC, unexpected dimer size compounds were observed by GC-MS. Dimers and trimers were observed by ESI MS. ESI tandem mass spectrometry was used to select plausible structures for the dimer. ESI MS with or without liquid chromatographic separation is useful for observing oligomeric byproducts with low volatility produced in organic reactions.
575 - 578
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