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Electron ionization-induced fragmentation of N- and O-alkoxymethylated carbostyril and phenanthridinone

✍ Scribed by Rafał Szmigielski; Witold Danikiewicz

Book ID
102378516
Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
377 KB
Volume
39
Category
Article
ISSN
1076-5174

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✦ Synopsis

Abstract

Unimolecular fragmentation patterns of N‐alkoxymethylated carbostyril and phenanthridinone and their O‐alkoxymethyl isomers were studied. The main fragmentation reaction observed for the studied compounds is the elimination of an aldehyde molecule. The main products of this reaction are the appropriate N‐methyl derivatives, but ions with other structures are also formed. This reaction is supposed to proceed via 1,3‐H shift in the alkoxymethyl group in the case of the N‐alkoxymethyl derivatives and by a multi‐step mechanism for O‐alkoxymethylated compounds. Another important fragmentation common for all studied compounds is the loss of an alkyl radical from N‐ and O‐alkoxymethyl groups, yielding the appropriate stable isomeric cations, which, according to the results of the further fragmentation, undergo fast equilibration reaction via an ion–neutral complex. This process is accompanied by the unusually high kinetic energy release value. Copyright © 2004 John Wiley & Sons, Ltd.

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